Dimethyl Sulfoxide → 3-Formyl-3-n-propyloxetane

HRID 1491604노트

반응식

HRID 1491604 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]1([CH2:17][CH2:18][CH3:19])[CH2:16][O:15][CH2:14]1.C(N(CC)CC)C>ClCCl.O>[CH:12]([C:13]1([CH2:17][CH2:18][CH3:19])[CH2:16][O:15][CH2:14]1)=[O:11]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1838902-Propyl-2-oxetanemethanol

생성물 1

HCID 150219983-Formyl-3-n-propyloxetane수율 106.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

A solution of dimethyl sulphoxide (12 ml) in dry dichloromethane (4.0 ml) was added to a solution of oxalyl chloride (7.4 ml) in dichloromethane (25 ml) stirred at -70° under nitrogen. After the addition was complete the resulting mixture was stirred for a further 5 minutes at -70° before a solution of 3-hydroxymethyl-3-n-propyloxetane (10.0 g) in dichloromethane (25 ml) was added, dropwise, over 10 minutes. The resulting mixture was allowed to stir for a further 30 minutes when neat triethylamine (54 ml) was added over approximately 30 minutes. The reaction mixture was allowed to warm to room temperature over 3 hours when it was poured into water. The organic phase was separated and the aqueous layer further extracted with fresh dichloromethane. The combined organic extracts were washed with dilute hydrochloric acid, saturated sodium bicarbonate and brine. The resulting organic phase was dried over anhydrous magnesium sulphate and evaporated in vacuo to give 3-formyl-3-n-propyloxetane (10.5 g) as a yellow oil.

후처리

  1. additionAfter the addition
  2. additionwas added
  3. additionwas added over approximately 30 minutes
  4. customThe organic phase was separated
  5. extractionthe aqueous layer further extracted with fresh dichloromethane
  6. washThe combined organic extracts were washed with dilute hydrochloric acid, saturated sodium bicarbonate and brine
  7. dry with materialThe resulting organic phase was dried over anhydrous magnesium sulphate
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-94cdcfd6ae3d43c3bddcf61845fce3f8
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371075

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