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

HRID 514636ノート

反応式

HRID 514636 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4c41fb8b60744160934cb0e56417f33b
出典データセット
uspto-grants-2015_08
特許番号
US09107964B2

反応ノート

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