Diethyl Ether → (3R,7R)-3,7,11-trimethyldodecyl p-toluenesulfonate

HRID 580371노트

반응식

HRID 580371 반응식
[CH3:1][C@H:2]([CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:3][CH2:4][OH:5].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.CCOCC>N1C=CC=CC=1>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:5][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:25])=[O:24])=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 1590641-Dodecanol, 3,7,11-trimethyl-, (R*,R*)-

생성물 1

HCID 10317779(3R,7R)-3,7,11-trimethyldodecyl p-toluenesulfonate수율 94.9%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of 10.44 g (45.8 mmol) of (3R,7R)-3,7,11-trimethyldodecan-1-ol in 150 mL of anhydrous pyridine was stirred in an acetone-ice bath while 17.4 g (91.3 mmol) of p-toluenesulfonyl chloride was added in one portion. The mixture was stirred in the acetone-ice bath for 2 hr then kept at 0° C. for 40 hr before being quenched by the addition of 300 mL of ice-water. The product was isolated by extraction with 3×300 mL of ether. The ether extracts were combined, washed with 400 mL of cold 3N HCl and saturated brine, then dried (MgSO4), filtered and concentrated in vacuo. There was obtained 16.6 g (94.9%) of (3R,7R)-3,7,11-trimethyldodecyl p-toluenesulfonate.

후처리

  1. additionwas added in one portion
  2. custombefore being quenched by the addition of 300 mL of ice-water
  3. customThe product was isolated by extraction with 3×300 mL of ether
  4. washwashed with 400 mL of cold 3N HCl and saturated brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-45e15b4db4544279b2942e1e96fe1c5c
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04752646

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