Water → 3-(4-{[4-(2-Ethoxycarbonyl-2-methylpropyl)-phenyl]-hydroxymethyl}-phenyl)-2,2-dimethylpropionic acid ethyl ester

HRID 2057198Notes

Reaction equation

HRID 2057198 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]([CH3:31])([CH3:30])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:29])[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)[CH3:2].[BH4-].[Na+].O.ClCCl>CO>[CH2:1]([O:3][C:4](=[O:32])[C:5]([CH3:30])([CH3:31])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:23])[CH3:22])=[CH:18][CH:19]=2)[OH:29])=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 666170323-{4-[4-(2-Ethoxycarbonyl-2-methylpropyl)-benzoyl]-phenyl}-2,2-dimethyl-propionic acid ethyl ester

Product 1

HCID 666172073-(4-{[4-(2-Ethoxycarbonyl-2-methylpropyl)-phenyl]-hydroxymethyl}-phenyl)-2,2-dimethylpropionic acid ethyl esterYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-{4-[4-(2-ethoxycarbonyl-2-methylpropyl)-benzoyl]-phenyl}-2,2-dimethyl-propionic acid ethyl ester (4.40 g, 10.0 mmol) in methanol (80 mL) was cooled in an ice-water bath. Sodium borohydride (0.45 g, 13.7 mmol) was added and the mixture was stirred for 5 h. Water (150 mL) and dichloromethane (65 mL) were added and the layers were separated. The aqueous layer was washed with dichloromethane (2×65 mL). The combined organic layers were washed with saturated NaCl solution (100 mL), dried over MgSO4, and concentrated under vacuum. The residue was subjected to column chromatography on silica using hexanes/ethyl acetate (9:1 and 6:1) as eluent to afford 3-(4-{[4-(2-ethoxycarbonyl-2-methylpropyl)-phenyl]-hydroxymethyl}-phenyl)-2,2-dimethylpropionic acid ethyl ester (3.63 g, 82%) as a colorless oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 7.24 (d, 4H, J=8.0 Hz), 7.07 (d, 4H, J=8.0 Hz), 5.77 (s, 1H), 4.08 (q, 4H, J=7.1 Hz), 2.83 (s, 4H), 2.62 (s, 1H), 1.21 (t, 6H, J=7.1 Hz), 1.16 (s, 12H). 13C NMR (75 MHz, CDCl3=77.23 ppm): δ (ppm): 177.6, 142.2, 137.3, 130.3, 126.3, 75.9, 60.5, 46.0, 43.4, 25.1, 14.3. HRMS (LSIMS, nba): Calcd for C27H35O4 (M+H−H2O): 423.2535, found: 423.2520.

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with dichloromethane (2×65 mL)
  3. washThe combined organic layers were washed with saturated NaCl solution (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e30194e3f30e48dda3ba24bcea47cea6
Source dataset
uspto-grants-2008_02
Patent number
US07335799B2

Reaction notes

Loading…