Water → 2-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-

HRID 2551

반응식

HRID 2551 반응식
[Si:1]([O:8][CH:9]1[CH2:13][CH:12]([O:14]C(=O)C)[CH:11]=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.[OH-].[Li+].O>C1COCC1.CO.O>[Si:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([OH:14])[CH:11]=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 127633543-Acetoxy-5-t-butyldimethylsiloxycyclopent-1-ene

생성물 1

HCID 101767472-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-수율 92%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

Dissolve (-)-acetic acid 4-tert-butyldimethylsilyloxy-cyclopent-2-enyl ester (2.3 mmol, prepared in example 10) in THF/methanol/water (2.7/0.9/0.9 mL). Add lithium hydroxide monohydrate (2.5 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 20% ethyl acetate/hexane) to provide the title compound (452 mg, 92% yield) [α]20D =+21.8°, (c=1.02, chloroform).

후처리

  1. additiondilute
  2. extractionextract with tert-butyl methyl ether
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify the residue by flash chromatography (silica gel, 20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-b7d46a26dfbe492a852ae078a89b028a
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728899

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