2-Heptanone, 1-(triphenylphosphoranylidene)- → 2-(7-Hydroxyheptyl)-3-(3-oxo-1-octenyl)cyclopentanol

HRID 1581092ノート

反応式

HRID 1581092 の反応式
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH:3]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].[C:17]([CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O1CCCC1>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:3]1[CH:4]([CH:7]=[CH:24][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:5][CH2:6][CH:2]1[OH:1]

参加物

4

反応物 2

HCID 107619442-Heptanone, 1-(triphenylphosphoranylidene)-HCID 215614973-Hydroxy-2-(7-hydroxyheptyl)cyclopentane-1-carbaldehyde

生成物 1

HCID 737960592-(7-Hydroxyheptyl)-3-(3-oxo-1-octenyl)cyclopentanol収率 63%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 3-hydroxy-2-(7-hydroxyheptyl)cyclopentanecarbaldehyde (4.5 g., 0.02 mole) and hexanoylmethylene triphenylphosphorane (7.5 g., 0.02 mole) in dry tetrahydrofuran (100 ml.) was heated under reflux for 6 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel. Elution with a 3:2 mixture of petrol (b.p. 40°-60°C.) and ethyl acetate gave 2-(7-hydroxyheptyl)-3-(3-oxo-1-octenyl)cyclopentanol (4 g., 63%), λmax 230 mμ, ε 12,900 (ethanol), νmax 1660 cm-1, 1620 cm-1 (liquid film).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel
  5. washElution
  6. additionwith a 3:2 mixture of petrol (b.p. 40°-60°C.) and ethyl acetate

出典と根拠

ORDレコード
ord-650faa6d3108440898981a376dac7454
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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