Hydrofluoric Acid → 3-(5-Hydroxypent-1-yl)cyclopentene

HRID 1722368노트

반응식

HRID 1722368 반응식
CC([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH:14]=[CH:13]1)(C)C.F.C(=O)(O)[O-].[Na+]>C(#N)C>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH:14]=[CH:13]1

참가 물질

5

반응물 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 139240733-(5-[(1,1-Dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene

생성물 1

HCID 150530153-(5-Hydroxypent-1-yl)cyclopentene

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

3-(5-[(1,1-Dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene (300 g, 1.170 moles) is diluted with acetonitrile (3000 ml) and a 40% stock solution of hydrofluoric acid (166 ml) is added. The reaction is stirred at room temperature for 10 minutes and then slowly neutralized with a saturated solution of sodium bicarbonate. The reaction is partitioned between ether (1500 ml) and the aqueous phase extracted with ether (1×1000 ml). The organic layers are combined and the solvent volume is reduced under vacuum. The residue is dried over anhydrous sodium sulfate and the remaining solvent removed leaving a clear, colorless oil. The product is kugelrohred under vacuum leaving a product sufficiently pure for the next reaction (171 g, 1.11 moles).

후처리

  1. customThe reaction is partitioned between ether (1500 ml)
  2. extractionthe aqueous phase extracted with ether (1×1000 ml)
  3. dry with materialThe residue is dried over anhydrous sodium sulfate
  4. customthe remaining solvent removed
  5. customleaving a clear, colorless oil
  6. customleaving a product
  7. customsufficiently pure for the next reaction (171 g, 1.11 moles)

출처 및 근거

ORD 기록
ord-c7c854de303a40afb6ec6c10ee40d0d9
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04855322

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