methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate → HCID 19004348, compound

HRID 2225803Notes

Reaction equation

HRID 2225803 reaction equation
C[O:2][C:3](=O)/[CH:4]=[CH:5]/[C:6]1[N:7]([CH:22]([CH3:24])[CH3:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.[H-].C([Al+]CC(C)C)C(C)C>ClCCl.C1(C)C=CC=CC=1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH:22]([CH3:23])[CH3:24])[C:6]=2/[CH:5]=[CH:4]/[CH2:3][OH:2])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 11221407methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19004348HCID 19004348, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

As in Example 227, (E)-3-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-2-propenoic acid methyl ester (4.43 g) in dry dichloromethane (60 mL) was treated with diisobutylaluminum hydride in toluene (1.5M; 30 mL) at -65° C. for 1 hour, then was worked up as previously described to give 4.15 g of (E)-3-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-2-propen-1-ol as a yellow oil. A portion (0.2 g) was purified by chromatography over silica gel (diethyl ether-hexane; 1:19) to furnish 0.175 g of the analytically pure alcohol as an oil.

Sources & evidence

ORD record
ord-fe112f939a6d495da02cfe3fcfbb9090
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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