Triethylamine → HCID 54129048, compound

HRID 376902Notes

Reaction equation

HRID 376902 reaction equation
ClC(OCC)=O.[CH:7]([C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[S:19]([CH3:22])(=[O:21])=[O:20])([CH3:9])[CH3:8].C(N(CC)CC)C>C1COCC1>[CH:7]([C:10]1[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][C:11]=1[S:19]([CH3:22])(=[O:20])=[O:21])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 106339154-Isopropyl-3-methylsulfonylbenzoic acid

Product 1

HCID 54129048HCID 54129048, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.3 g of ethyl chloroformate dissolved in 5 ml of THF were added dropwise at -10° C. to a solution of 4.8 g of 4-isopropyl-3-methylsulfonylbenzoic acid and 2.1 g of triethylamine in 40 ml of THF. After stirring for 1 hour, the precipitate which was deposited was filtered off with suction, and the filtrate was added dropwise to a solution of 2.3 g of sodium borohydride in 25 ml of water. The reaction mixture was subsequently stirred for 5 h, acidified with hydrochloric acid and extracted with ether, and the organic phase was washed with 10 percent sodium hydroxide solution. After concentrating, 3.1 g of 4-isopropyl-3-methylsulfonylbenzyl alcohol were obtained.

Workup

  1. filtrationthe precipitate which was deposited was filtered off with suction
  2. additionthe filtrate was added dropwise to a solution of 2.3 g of sodium borohydride in 25 ml of water
  3. stirringThe reaction mixture was subsequently stirred for 5 h
  4. extractionextracted with ether
  5. washthe organic phase was washed with 10 percent sodium hydroxide solution
  6. concentrationAfter concentrating

Sources & evidence

ORD record
ord-654bd25a9bdd472d9ab0728b51191f1d
Source dataset
uspto-grants-2000_02
Patent number
US06022899

Reaction notes

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