1,7-Heptanediol → 7-Trimethylsiloxy-1-heptanol

HRID 399325노트

반응식

HRID 399325 반응식
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[H-].[Na+].[Si:12](Cl)([C:15](C)(C)C)([CH3:14])[CH3:13]>C1COCC1>[CH3:13][Si:12]([CH3:15])([CH3:14])[O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:9]

참가 물질

5

반응물 3

HCID 123811,7-HeptanediolHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 189709087-Trimethylsiloxy-1-heptanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1,7-heptandiol (44 mmol) in THF (15 mL) is cooled to 0° C. and treated with sodium hydride (44 mmol) followed by tert-butyldimethylsilyl chloride (44 mmol). The reaction mixture is stirred at room temperature overnight. Concentration in vacuo and flash chromatography affords 7-trimethylsiloxy-1-heptanol. To a solution of 7-trimethylsiloxy-1-heptanol (11.6 mmol) in dry dichloromethane (50 mL) is added 2,6-di-tert-butyl-4-methylpyridine (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 7-trimethylsiloxy-1-heptyl triflate (50) which is used without further purification.

후처리

  1. concentrationConcentration in vacuo and flash chromatography

출처 및 근거

ORD 기록
ord-0cbe16c4062d4aca9ef3f81eef869160
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817879

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