Acetic Anhydride → 1-Acetyl-1H-indol-3-yl acetate

HRID 582653

반응식

HRID 582653 반응식
[C:1]1([N:7]([C:12]([OH:14])=O)[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]([O-:18])=O.[Na+].[CH3:20]C(OC(C)=O)=O>CN(C=O)C>[C:12]([N:7]1[C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]([O:11][C:16](=[O:18])[CH3:15])=[CH:8]1)(=[O:14])[CH3:20]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 53420527HCID 53420527, 화합물

생성물 1

HCID 5836021-Acetyl-1H-indol-3-yl acetate수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of phenylglycine-o-carboxylic acid obtained in Example 30 (2.30 g, 11.8 mmol) and NaOAc (3.75 g, 47.1 mmol) in DMF (29 mL) was slowly added Ac2O (11.7 mL, 118 mmol) and the mixture was refluxed for 2 hours. After cooling, the mixture was concentrated to 10 mL, partitioned between H2O (60 mL) and CHCl3 (120 mL), and the aqueous layer was extracted with CHCl3 (3×). The combined organics were washed with Na2CO3 (1 M), H2O, brine and dried (MgSO4). Purification of the crude oil by LPLC, eluting with hexane-EtOAc (2:1), afforded 1.89 g (74%) of the title compound as a light yellow powder, Rf 0.34 (hexane-EtOAc 2:1), mp 79.6-80.5° C.; 1H NMR (CDCl3) δ 8.47 (d, J=8.0, 1H), 7.72 (s, 1H), 7.55 (d, J=8.0, 1H), 7.40 (t, J=8.0, 1H), 7.31 (t, J=8.0, 1H), 2.62 (s, 3H), 2.40 (s, 3H), 13C NMR (CDCl3) δ 168.7, 167.8, 134.6, 132.8, 126.2, 123.7, 123.6, 117.4, 116.7, 113.3, 23.9, 21.0; MS (EI, m/z) 217 (M+)

후처리

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated to 10 mL
  4. custompartitioned between H2O (60 mL) and CHCl3 (120 mL)
  5. extractionthe aqueous layer was extracted with CHCl3 (3×)
  6. washThe combined organics were washed with Na2CO3 (1 M), H2O, brine
  7. dry with materialdried (MgSO4)
  8. customPurification of the crude oil by LPLC
  9. washeluting with hexane-EtOAc (2:1)

출처 및 근거

ORD 기록
ord-8efd5bb1a71f40d1af1279bb09205739
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925647

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