Lithium Hydroxide → [4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic Acid

HRID 15721노트

반응식

HRID 15721 반응식
C([O:3][C:4](=[O:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:20][C:19]3[C:18]([O:21][CH2:22][CH3:23])=[C:17]4[CH:24]=[CH:25][CH:26]=[CH:27][C:16]4=[C:15]([O:28][CH2:29][CH3:30])[C:14]=3[CH2:13]2)=[CH:8][CH:7]=1)C.[OH-].[Li+]>O1CCCC1.O>[CH2:22]([O:21][C:18]1[C:19]2[CH2:20][N:12]([C:9]3[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:31])=[O:3])=[CH:11][CH:10]=3)[CH2:13][C:14]=2[C:15]([O:28][CH2:29][CH3:30])=[C:16]2[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=12)[CH3:23]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 131726211ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

생성물 1

HCID 21079276[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic Acid수율 43%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate (10 mg, 0.024 mmol) in tetrahydrofuran (4 ml) and a solution of lithium hydroxide (6 mg, 0.24 mmol) in water (1 ml) were stirred vigorously for 14 h. The reaction mixture was diluted with water (10 ml) and extracted with ethyl acetate (2×5 ml) and the organic extracts discarded. The aqueous phase was acidified with 2N hydrochloric acid to pH=5 and extracted with ethyl acetate (3×5 ml). The combined organic extracts were dried over magnesium sulphate and the solvent removed in vacuo to give the product as a red solid (4 mg, 43%). δH CDCl3 8.13 (2H, dd, J=6.5, 3.2), 7.49, (2H, dd, J=6.5, 3.2), 7.24 (2H, d, 8.3), 6.75 (2H, d, J=8.3), 4.81 (4H, s), 4.19 (4H, q, J=7.0), 3.69 (2H, s), 1.53 (6H, t, J=7.0); LC retention time 3.92 min, ms 392, [MH+].

후처리

  1. extractionextracted with ethyl acetate (2×5 ml)
  2. extractionextracted with ethyl acetate (3×5 ml)
  3. dry with materialThe combined organic extracts were dried over magnesium sulphate
  4. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-d6f642dc4afa440cadc7dffc7c3543a3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732622B2

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