Benzyl mercaptan → HCID 57201698, compound

HRID 1534753Notes

Reaction equation

HRID 1534753 reaction equation
[H-].[K+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][C:12]1[C:13]([N+]([O-])=O)=[C:14]([CH:21]=[CH:22][CH:23]=1)[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16]>O1CCCC1>[CH3:11][C:12]1[C:13]([S:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[C:14]([CH:21]=[CH:22][CH:23]=1)[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 82127Potassium hydrideHCID 524488701-Methylethyl 3-methyl-2-nitrobenzoate

Product 1

HCID 57201698HCID 57201698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of dry tetrahydrofuran (125mL) and 35% potassium hydride in oil (6.3 g) was slowly added benzyl mercaptan (6.1 mL) at 0° C. under an inert atmosphere. After 15 minutes, 3-methyl-2-nitrobenzoic acid, 1-methylethyl ester (11.23 g) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between 6N sodium hydroxide (25 mL) and ethyl acetate (150 mL). The organic phase was dried over magnesium sulfate, filtered, concentrated, and chromatographed on silica gel eluted with 5% ethyl acetate in hexanes to give 13.7 g of the title compound as a yellow oil, nD 1.5642.

Workup

  1. customat 0° C.
  2. customThe reaction mixture was partitioned between 6N sodium hydroxide (25 mL) and ethyl acetate (150 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel
  7. washeluted with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-23829148d39d40df96058b75d1170e73
Source dataset
uspto-grants-1992_02
Patent number
US05090993

Reaction notes

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