4-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman → 4-(9-Hydroxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1859293Notes

Reaction equation

HRID 1859293 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]1(O)[C:23]2[CH:24]=[CH:25][C:26]([O:28][CH2:29][O:30][CH3:31])=[CH:27][C:22]=2[O:21][CH2:20][C:19]1([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=1)[CH3:32])(C(C)(C)C)(C)C>C(OCC)(=O)C.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]1[C:23]2[CH:24]=[CH:25][C:26]([O:28][CH2:29][O:30][CH3:31])=[CH:27][C:22]=2[O:21][CH2:20][C:19]1([C:33]1[CH:34]=[CH:35][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:37][CH:38]=1)[CH3:32]

Participants

4

Reactant 1

HCID 220330974-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Product 1

HCID 154817594-(9-Hydroxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3RS,4RS)-4-[9-(t-Butyldimethylsilyloxy)nonynyl]-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran (340 mg, 0.56 mmol) was dissolved in ethyl acetate (10 ml) and then 10% Pd/C (180 mg) was added dropwise thereto. The reaction solution was stirred for 15 hours under hydrogen atmosphere, filtered and then concentrated. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1→1:1) to obtain 90 mg (yield: 33%) of the title compound as a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6a7759915b244478a68c923986dd0097
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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