Acetic Acid → 3-Hydroxy-2-(7-hydroxyheptyl)cyclopentane-1-carbaldehyde

HRID 1581091ノート

反応式

HRID 1581091 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[C:23](=[O:24])[CH2:22][CH2:21][CH:20]1[C:25]#N.C(O)(=[O:29])C>C1C=CC=CC=1.C(OCC)C>[OH:24][CH:23]1[CH2:22][CH2:21][CH:20]([CH:25]=[O:29])[CH:19]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][OH:11]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 205429242-(7-Hydroxyheptyl)-3-oxocyclopentanecarbonitrileHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 215614973-Hydroxy-2-(7-hydroxyheptyl)cyclopentane-1-carbaldehyde収率 43%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒

実験手順

A solution of diisobutylaluminium hydride (25.6 g., 0.18 mole) in benzene (250 ml.) was added, with rapid stirring, to a solution of 2-(7-hydroxyheptyl)-3-oxocyclopentanecarbonitrile (10 g., 0.045 mole) in dry diethyl ether (250 ml.) at 10°-15°C. Stirring at ambient temperature was contined for 15 minutes and the mixture was added to 2N aqueous acetic acid (300 ml.) at a temperature lower than 15°C. The organic phase was separated and the aqueous layer was extracted with diethyl ether. The combined organic phases were washed with aqueous sodium bicarbonate, dried over magnesium sulphate and the solvents were removed in vacuo. The residue was distilled under reduced pressure to give 3-hydroxy-2-(7-hydroxyheptyl)cyclopentanecarbaldehyde (4.5 g., 43%), b.p. 185°-193°C./0.1 mm.Hg, nD22.5 1.4995.

後処理

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. washThe combined organic phases were washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulphate
  5. customthe solvents were removed in vacuo
  6. distillationThe residue was distilled under reduced pressure

出典と根拠

ORDレコード
ord-d2705bb4163b4fce89e06ab71bbba00b
出典データセット
uspto-grants-1976_01
特許番号
US03935261

反応ノート

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