Lithium hydroxide, monohydrate → 3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoic acid

HRID 548661

반응식

HRID 548661 반응식
O.[OH-].[Li+].[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@@H:23]([CH3:36])[CH2:24][O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:21]=1)[C:15]([O:17]C)=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.C1COCC1>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@@H:23]([CH3:36])[CH2:24][O:25][Si:26]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:33]([CH3:35])[CH3:34])[CH:21]=1)[C:15]([OH:17])=[O:16])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 53629622methyl 3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoate

생성물 1

HCID 536296213-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoic acid수율 100.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
43 °C

실험 절차

Lithium hydroxide monohydrate (12.14 g, 0.289 mol) in water (100 mL) was added to a solution of methyl 3-(benzyloxy)-5-{(s)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoate (62 g, 0.131 mol) in THF (300 mL) and warmed to 43° C. The reaction was stirred for 16 hours, the THF removed in vacuo and the resultant mixture acidified to pH 5 with 10% w/v citric acid. This was extracted with ethyl acetate (2×300 mL) and the combined organic layers were dried (MgSO4), filtered and evaporated to afford the title compound (60.2 g).

후처리

  1. customthe THF removed in vacuo
  2. extractionThis was extracted with ethyl acetate (2×300 mL)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-d4e0e0099c8540e59429b65cf2e4bf07
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943607B2

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