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Methanol → 5-[4-(4,6-Dihydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

HRID 1589693
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HRID 1589693 반응식
[BH4-].[Na+].[OH:3][C:4]1[C:5]([CH3:34])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:20]=1)([CH3:16])[CH2:8][C:7]2=[O:33].CO.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[OH:33][CH:7]1[C:6]2[C:11](=[C:12]([CH3:15])[C:13]([CH3:14])=[C:4]([OH:3])[C:5]=2[CH3:34])[O:10][C:9]([CH2:17][O:18][C:19]2[CH:32]=[CH:31][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:20]=2)([CH3:16])[CH2:8]1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 98252415-[4-(6-Hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

생성물 1

HCID 136058355-[4-(4,6-Dihydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

시약·촉매·용매 1

HCID 176
Acetic Acid
용매

실험 절차

450 mg of sodium borohydride were added to a mixture of 278 mg of 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Example 22) and 9 ml of methanol, and the resulting mixture was stirred at room temperature for 2 hours. Then, a 1% w/v aqueous solution of acetic acid was added to the reaction mixture, and the mixture was neutralized with an aqueous solution of potassium carbonate and extracted with ethyl acetate. The ethyl acetate solution was washed with water and dried over anhydrous sodium sulfate. Ethyl acetate was distilled off from the mixture under reduced pressure, and the resulting residue was subjected to silica gel column chromatography, eluted with a 5:3 by volume mixture of hexane and ethyl acetate, to yield 5-[4-(4,6-dihydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione. Its melting point was 102°-118° C.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationEthyl acetate was distilled off from the mixture under reduced pressure
  5. washeluted with a 5:3 by volume mixture of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-8e30e67b54da4d3ea119b01ffb376c04
출처 데이터셋
uspto-grants-1986_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04572912

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