4-[4-(t-Butyl dimethylsilyloxy)-1-butynyl]4-hydroxy-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman → (3RS,4RS)-4-[4-(t-butyldimethylsilyloxy)-1-butyl]-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman

HRID 1792362Notes

Reaction equation

HRID 1792362 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1(O)[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=2)[O:16][CH2:15][C:14]1([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=1)[CH3:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=2)[O:16][CH2:15][C:14]1([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:32][CH:33]=1)[CH3:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 220334204-[4-(t-Butyl dimethylsilyloxy)-1-butynyl]4-hydroxy-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman

Product 1

HCID 22033330(3RS,4RS)-4-[4-(t-butyldimethylsilyloxy)-1-butyl]-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchromanYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-[4-(t-butyl dimethylsilyloxy)-1-butynyl]4-hydroxy-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (1.6 g, 2.95 mmol) was dissolved in ethyl acetate (30 ml), and then 10% Pd/C (0.6 g) was added thereto. The reaction suspension was stirred under hydrogen for 1 hour, filtered, and concentrated. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=20:1) to give the title compound (680 mg, yield 44%) as a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a7b88fd5bae64d6f9748f798e29b7a11
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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