Water → 7-[2-(3-Hydroxy-3-methyloct-1-enyl)-5-oxocyclopentyl]heptanol

HRID 2052330노트

반응식

HRID 2052330 반응식
[OH:1][C:2]([CH3:31])([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH:6]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][Si](C)(C)C.O.C1(C)C=CC=CC=1>C(O)(=O)C.O1CCOCC1>[OH:1][C:2]([CH3:31])([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7](=[O:8])[CH:6]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]

참가 물질

6

반응물 3

HCID 962WaterHCID 1140TolueneHCID 537744147-(3-Hydroxy-3-methyloct-1-enyl)-6-(7-trimethylsiloxyheptyl)-1,4-dioxaspiro[4,4]nonane

생성물 1

HCID 542592447-[2-(3-Hydroxy-3-methyloct-1-enyl)-5-oxocyclopentyl]heptanol수율 32.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 312751,4-Dioxane용매

실험 절차

7-(3-Hydroxy-3-methyloct-1-enyl)-6-(7-trimethylsiloxyheptyl)-1,4-dioxaspiro[4,4]nonane [0.5 g; prepared as hereinbefore described in Example 3(iii)], water (10 ml.) and glacial acetic acid (20 ml.) were left to stand together at room temperature for 6 hours. The solution was then evaporated in vacuo at a temperature below 50° C. Ethyl acetate (150 ml.) was added to the residue and the resulting solution was washed with water until the pH of the washings was 5, dried over sodium sulphate, and evaporated to give a crude product (0.37 g.). The crude product was subjected to preparative thin layer chromatography on silica gel, using a mixture of toluene, dioxan and acetic acid (65:15:1 by volume) as eluant, eluting twice, to give 7-[2-(3-hydroxy-3-methyloct-1-enyl)-5-oxocyclopentyl]heptanol (0.12 g.).

후처리

  1. customThe solution was then evaporated in vacuo at a temperature below 50° C
  2. additionEthyl acetate (150 ml.) was added to the residue
  3. washthe resulting solution was washed with water until the pH of the washings
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto give a crude product (0.37 g.)
  7. washeluting twice

출처 및 근거

ORD 기록
ord-21050184abd740a58aedd8a49c41da04
출처 데이터셋
uspto-grants-1980_01
특허 번호
US04183870

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