Propyl mercaptan → HCID 86746796, compound

HRID 248072Notes

Reaction equation

HRID 248072 reaction equation
[H-].[Li+].C(S)CC.[CH3:7][C:8]([CH3:28])([O:10][C:11](=[O:27])[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([CH2:25][CH3:26])[C:21]([O:23]C)=[O:22])[CH3:9]>CN(C)P(N(C)C)(N(C)C)=O>[CH3:28][C:8]([CH3:9])([O:10][C:11](=[O:27])[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([CH2:25][CH3:26])[C:21]([OH:23])=[O:22])[CH3:7]

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 62714Lithium hydrideHCID 86746797HCID 86746797, compound

Product 1

HCID 86746796HCID 86746796, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

Suspend lithium hydride (1.01 g, 126.4 mmol) in hexamethylphosphoramide (50 mL) and treat with 1-propanethiol (11.5 mL, 126.4 mmol). Stir for 1.5 hours and add to a solution of 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]thio-alpha-ethyl-benzeneacetic acid, methyl ester (5.85 g, 18.06 mmol) in hexamethylphosphoramide (50 mL) under a nitrogen atmosphere. Stir for 20 hours and pour into ice cold 5% hydrochloric acid (500 mL). Extract into ethyl ether (4×300 mL), wash with water (500 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography to give the title compound.

Workup

  1. stirringStir for 20 hours
  2. extractionExtract into ethyl ether (4×300 mL)
  3. washwash with water (500 mL)
  4. dry with materialdry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by flash chromatography

Sources & evidence

ORD record
ord-8d16b6e2cf794b9b9438122370fed1ca
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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