Methanol → [2-Methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-phenyl-acetic acid methyl ester

HRID 346847Notes

Reaction equation

HRID 346847 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([O:20][Si](CC)(CC)CC)([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[CH:8]=2)N1.[Na].CC[O:31][CH2:32][CH3:33].[NH4+:34].[Cl-].[CH3:36][OH:37]>>[CH3:36][O:37][C:32](=[O:31])[CH:33]([N:34]1[C:4]2[C:9](=[CH:8][C:7]([C:11]([OH:20])([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:19])[F:18])=[CH:6][CH:5]=2)[CH2:10][CH:2]1[CH3:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 210822122-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indole

Product 1

HCID 11583177[2-Methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-phenyl-acetic acid methyl ester

Conditions

Temperature
100 °C

Procedure

A solution of 0.14 g (0.34 mmol) 2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indole (example 51.2) in 1.5 mL of methanol was treated with 0.028 g (0.34 mmol) of sodium actetate and 0.053 mL (0.34 mmol) of α-bromophenyl methyl acetate. The mixture was stirred at 100° C. in a pressure tube for 10 hrs and then distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 4:1 yielded 170 mg of [2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-phenyl-acetic acid methyl ester, colourless viscous oil, MS: 448 (MH+).

Workup

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customevaporated

Sources & evidence

ORD record
ord-6ebf8e44c8b3467eb761e1f3cd39f6b3
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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