5-Benzyloxyethyl-2,2-dimethyl-5-(t-butyldiphenylsiloxymethyl)-1,3-dioxane → 5-(t-Butyldiphenylsiloxymethyl)-2,2-dimethyl-5-hydroxyethyl-1,3-dioxane

HRID 514636노트

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HRID 514636 반응식
C([O:8][CH2:9][CH2:10][C:11]1([CH2:19][O:20][Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13][CH2:12]1)C1C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[O:20]([CH2:19][C:11]1([CH2:10][CH2:9][OH:8])[CH2:12][O:13][C:14]([CH3:18])([CH3:17])[O:15][CH2:16]1)[Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

4

반응물 1

HCID 903004385-Benzyloxyethyl-2,2-dimethyl-5-(t-butyldiphenylsiloxymethyl)-1,3-dioxane

생성물 1

HCID 903004895-(t-Butyldiphenylsiloxymethyl)-2,2-dimethyl-5-hydroxyethyl-1,3-dioxane수율 26.3%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

570 mg (1.56 mmol equivalents) of 5-benzyloxyethyl-2,2-dimethyl-5-(t-butyldiphenylsiloxymethyl)-1,3-dioxane was dissolved in 30 mL of ethyl acetate, 100 mg of palladium carbon was added thereto under argon atmosphere, and the mixture was stirred under hydrogen atmosphere at room temperature (25° C.) for 22 hours. After completion of the reaction, a precipitate was filtered, and the filtrate was concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1) to give 174 mg (0.41 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-hydroxyethyl-1,3-dioxane.

후처리

  1. customAfter completion of the reaction
  2. filtrationa precipitate was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1)

출처 및 근거

ORD 기록
ord-4c41fb8b60744160934cb0e56417f33b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107964B2

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