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

HRID 442435노트

반응식

HRID 442435 반응식
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]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 20354863HCID 20354863, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
50 °C

실험 절차

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 (l) of 3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbonitrile without further purification.

후처리

  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

출처 및 근거

ORD 기록
ord-a444d76274dc49a49e741ae5e3d5fbd1
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04045467

반응 노트

불러오는 중…