Trifluoroacetic anhydride → (5-Methoxypyridin-2-yl)methanol

HRID 1095444노트

반응식

HRID 1095444 반응식
FC(F)(F)[C:3]([O:5][C:6](=O)[C:7](F)(F)F)=O.[NH:14]1[CH2:23]C2C(=CC=CC=2)[CH2:16][C@H:15]1[C:24](O)=[O:25]>ClCCl>[CH3:3][O:5][C:6]1[CH:7]=[CH:16][C:15]([CH2:24][OH:25])=[N:14][CH:23]=1

참가 물질

4

반응물 2

HCID 9845Trifluoroacetic anhydride2회HCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

생성물 1

HCID 12214020(5-Methoxypyridin-2-yl)methanol수율 64%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic anhydride (28.2 mL, 203 mmol) was added dropwise to an ice cooled solution of the product from preparation 20 (˜135 mmol) in dichloromethane (500 mL), the mixture was allowed to warm to room temperature and stirred overnight. Tic analysis indicated still largely starting material so a further portion of trifluoroacetic anhydride (15 mL, 108 mmol) was added dropwise and the mixture was allowed to stir for a further 27 hours. The reaction was quenched by the cautious addition of methanol (250 mL) and left to stir for 30 minutes before being concentrated in vacuo. 2.5 M sodium hydroxide (100 mL) was then added cautiously and the mixture was extracted with dichloromethane (4×100 mL). The combined organic extracts were dried (MgSO4) and evaporated to give the desired product (12 g, 64%) contaminated with recovered starting material (˜15 mol %). 1H NMR (CDCl3, 400 MHz) δ 3.80 (3H, s), 4.40 (1H, br), 4.66 (2H, s), 7.16 (1H, dd), 7.20 (1H, d), 8.17 (1H, d).

후처리

  1. additionwas added dropwise
  2. stirringto stir for a further 27 hours
  3. customThe reaction was quenched by the cautious addition of methanol (250 mL)
  4. waitleft
  5. stirringto stir for 30 minutes
  6. concentrationbefore being concentrated in vacuo
  7. addition2.5 M sodium hydroxide (100 mL) was then added cautiously
  8. extractionthe mixture was extracted with dichloromethane (4×100 mL)
  9. dry with materialThe combined organic extracts were dried (MgSO4)
  10. customevaporated

출처 및 근거

ORD 기록
ord-641237bb9cbd438f8a921551e66aea7c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138188B2

반응 노트

불러오는 중…