Propyl mercaptan → HCID 86746793, compound

HRID 248069Notes

Reaction equation

HRID 248069 reaction equation
[H-].[Li+].C(S)CC.[CH3:7][C:8]([CH3:28])([O:10][C:11](=[O:27])[CH2:12][O: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][O: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 86746794HCID 86746794, compound

Product 1

HCID 86746793HCID 86746793, compoundYield 75.4%

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]oxy-alpha-ethyl-benzeneacetic acid, methyl ester (5.57 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 (5→10→20% isopropanol/hexane) to give the title compound (4.01 g).

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 (5→10→20% isopropanol/hexane)

Sources & evidence

ORD record
ord-50beeecd9f284f109677cfc734f09879
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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