Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [O-]CC.[Na+].[C:5]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:6][SH:7].[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16]Br)[CH3:13].O>C(O)C>[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16][S:7][CH2:6][C:5]([O:9][CH2:10][CH3:11])=[O:8])[CH3:13]
Reactant: CCOC(=O)CS
Reactant: CCOC(CBr)OCC
Agent: CC[O-]
Agent: [Na+]
Solvent: O
Solvent: CCO
Product: CCOC(=O)CSCC(OCC)OCC
Yield: 58.5 %

Procedure:
Sodium ethoxide (2.83 g) is added to a solution of ethyl thioglycolate (5.00 g) and bromoacetaldehyde diethylacetal (8.20 g) in ethanol (150 ml), and the mixture is refluxed for three hours. The reaction mixture is allowed to stand at room temperature, water is added to the mixture, and the whole is extracted with diethyl ether. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled reference compound (5.75 g).
Reaction SMILES: [CH2:1]([P:3](Cl)[CH2:4][CH3:5])[CH3:2].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Li])=[CH:11][CH:10]=1.IC1C=CC(OC)=CC=1>CCOCC>[CH2:1]([P:3]([CH2:4][CH3:5])[C:12]1[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=1)[CH3:2]
Reactant: [Li]c1ccc(OC)cc1
Reactant: CCP(Cl)CC
Agent: COc1ccc(I)cc1
Solvent: CCOCC
Product: CCP(CC)c1ccc(OC)cc1
Reaction time: 0.67 h

Procedure:
A solution of 10 g. (0.08 mole) of diethylphosphinous chloride in 100 ml. of ether was added to a solution of p-methoxyphenyllithium [prepared from 23.4 g. (0.1 mole) of p-iodoanisole in 100 ml. of ether and 62.5 ml. of 1.6 M n-butyllithium in hexane] under a nitrogen atmosphere. After 40 minutes, the reaction mixture was filtered and the solvent removed at reduced pressure. Distillation of the residual oil gave (diethyl) (p-methoxyphenyl)phosphine as a colorless liquid, b.p. 85°-90° C. at 0.5 mm.