Water → (1-Phenylcyclopentyl)methanol

HRID 977862

반응식

HRID 977862 반응식
[C:1]1([C:7]2([C:12](O)=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[C:1]1([C:7]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 661671-Phenylcyclopentanecarboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 123544(1-Phenylcyclopentyl)methanol수율 99.6%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

A solution of 1.15 g (6.04 mmol) of (1-phenylcyclopentyl)carboxylic acid in 10 ml of tetrahydrofuran was added dropwise over a period of 20 minutes to a suspension of 344 mg (9.06 mmol) of lithium aluminum hydride in 20 ml of tetrahydrofuran, whilst ice-cooling, and the resulting mixture was stirred for 30 minutes at 60° C. At the end of this time, the reaction mixture was again ice-cooled, and then 0.3 ml of water, 10 ml of a 2N aqueous solution of sodium hydroxide and 1 ml of water were added, in that order, and the resulting mixture was diluted with diethyl ether. The white gel material which appeared was filtered off, and then the filtrate was washed with water, with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 50 g of silica gel, using methylene chloride as the eluent, to give 1.06 g (yield 99%) of the title compound as colorless crystals.

후처리

  1. temperaturecooling
  2. temperaturecooled
  3. filtrationThe white gel material which appeared was filtered off
  4. washthe filtrate was washed with water, with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through 50 g of silica gel

출처 및 근거

ORD 기록
ord-7e57e22773584ea7b2d68a4f38f44cf4
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614550

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