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

HRID 514636Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-4c41fb8b60744160934cb0e56417f33b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107964B2

Reaction notes

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