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

HRID 2052330ノート

反応式

HRID 2052330 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-21050184abd740a58aedd8a49c41da04
出典データセット
uspto-grants-1980_01
特許番号
US04183870

反応ノート

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