Ethyl Acetate → 4-{4-[4-(Hydroxyethyloxy)phenyl]-1-butyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman

HRID 1792401Notes

Reaction equation

HRID 1792401 reaction equation
C([O:5][C:6]([CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][CH2:31][O:32][CH3:33])=[CH:27][CH:28]=3)[O:23][CH2:22][C:21]2([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:37][CH:36]=2)[CH3:34])=[CH:12][CH:11]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].C(OCC)(=O)C>O1CCCC1>[OH:5][CH2:6][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][CH2:31][O:32][CH3:33])=[CH:27][CH:28]=3)[O:23][CH2:22][C:21]2([C:35]2[CH:36]=[CH:37][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:39][CH:40]=2)[CH3:34])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 220330124-{4-[4-(t-Butoxycarbonylmethyloxy)phenyl]-1-butyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman

Product 1

HCID 695898584-{4-[4-(Hydroxyethyloxy)phenyl]-1-butyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchromanYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{4-[4-(t-butoxycarbonylmethyloxy)phenyl]-1-butyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman (744 mg, 1.226 mmol) in dry tetrahydrofuran (10 mi) was added lithium aluminum hydride (71.8 mg, 1.89 mmol) at 0° C. and stirred for 4 h at the room temperature. When the reaction was completed, 17% sodium hydroxide solution was added to the reaction solution until the white precipitate appeared, and then added ethyl acetate to the reaction mixture. The resulting mixture was filtered over celite and washed several times with ethyl acetate. The filtrate was concentrated under reduced pressure to give the title compound (658 mg, yield: quant.) as a colorless oil. The resulting compound was used in the next reaction without purification.

Workup

  1. filtrationThe resulting mixture was filtered over celite
  2. washwashed several times with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3ba945d069046049c5a08a5de0469e4
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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