Sodium borohydride → 3,4-Dihydroxy-2-(3-hydroxyoctyl)cyclopentane carbonitrile

HRID 372125ノート

反応式

HRID 372125 の反応式
C([O:4][CH:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:6][CH2:7][CH:8]1[CH:12]([C:13]#[N:14])[CH2:11][CH:10]([OH:15])[C:9]1=[O:16])(=O)C.[BH4-].[Na+]>CO.[OH-].[Na+]>[OH:16][CH:9]1[CH:10]([OH:15])[CH2:11][CH:12]([C:13]#[N:14])[CH:8]1[CH2:7][CH2:6][CH:5]([OH:4])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 20354863HCID 20354863、化合物

生成物 1

HCID 543134323,4-Dihydroxy-2-(3-hydroxyoctyl)cyclopentane carbonitrile収率 78.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
50 °C

実験手順

A stirred solution of 2-(3-acetoxyoctyl)-3-cyano-5-hydroxycyclopentanone (23.5 g.) [prepared as described in (j) above] in methanol (135 ml.) was treated dropwise, during 15 minutes, with a solution of sodium borohydride (13.2 g.) in 0.2N aqueous sodium hydroxide solution (70 ml.) at 15°-20° C. After 1 hour the solution was slowly heated to 50° C., stirred at 50° C. for 3 hours, and then allowed to stand at room temperature overnight. Methanol was removed in vacuo, water (75 ml.) was added and the mixture acidified by means of concentrated hydrochloric acid. The mixture was extracted with diethyl ether and the ethereal extract was washed with water, dried with magnesium sulphate and evaporated in vacuo to give crude 3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentane carbonitrile (16 g.), which was used in the following preparation (1) of 3,4di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbonitrile without further purification.

後処理

  1. waitto stand at room temperature overnight
  2. customMethanol was removed in vacuo, water (75 ml.)
  3. additionwas added
  4. extractionThe mixture was extracted with diethyl ether
  5. extractionthe ethereal extract
  6. washwas washed with water
  7. dry with materialdried with magnesium sulphate
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-cd53ed672cac4c039361e5d6d9b4bd54
出典データセット
uspto-grants-1978_05
特許番号
US04088821

反応ノート

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