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

HRID 1095444ノート

反応式

HRID 1095444 の反応式
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

参加物

4

反応物 2

HCID 9845Trifluoroacetic anhydride2 回HCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

生成物 1

HCID 12214020(5-Methoxypyridin-2-yl)methanol収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-641237bb9cbd438f8a921551e66aea7c
出典データセット
uspto-grants-2012_03
特許番号
US08138188B2

反応ノート

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