Water → 4-{4-[4-(t-Butoxycarbonylmethyloxy)phenyl]-1-butyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman

HRID 1792400Notes

Reaction equation

HRID 1792400 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][O:24][CH3:25])=[CH:19][CH:20]=3)[O:15][CH2:14][C:13]2([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][O:35][CH3:36])=[CH:29][CH:28]=2)[CH3:26])=[CH:4][CH:3]=1.[H-].[Na+].[C:39]([O:43][C:44](=[O:47])[CH2:45]Br)([CH3:42])([CH3:41])[CH3:40].O>O1CCCC1>[C:39]([O:43][C:44]([CH2:45][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][O:24][CH3:25])=[CH:19][CH:20]=3)[O:15][CH2:14][C:13]2([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][O:35][CH3:36])=[CH:31][CH:32]=2)[CH3:26])=[CH:4][CH:3]=1)=[O:47])([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 220333894-[4-(4-Hydroxyphenyl)-1-butyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman

Product 1

HCID 220330124-{4-[4-(t-Butoxycarbonylmethyloxy)phenyl]-1-butyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchromanYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(4-hydroxyphenyl)-1-butyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman (481 mg, 0.976 mmol) in dry tetrahydrofuran (8 ml) was added sodium hydride (22.7 mg, 1.418 mmol) at room temperature and stirred for 20 minutes. Bromoacetic acid tert-butylester (276.7 mg, 1.418 mmol) was added thereto at the same temperature and stirred for 20 minutes. After the reaction was completed, water was added to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 589 mg (yield: quant.) of the title compound as a colorless oil. The resulting compound was used in the next reaction without purification.

Workup

  1. stirringat the same temperature and stirred for 20 minutes
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb5613b1b5b74d26bc9c8f8102fa89da
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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