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

HRID 399325ノート

反応式

HRID 399325 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 189709087-Trimethylsiloxy-1-heptanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  1. concentrationConcentration in vacuo and flash chromatography

出典と根拠

ORDレコード
ord-0cbe16c4062d4aca9ef3f81eef869160
出典データセット
uspto-grants-1998_10
特許番号
US05817879

反応ノート

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