3-[1-(4-Chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethyl propanoic acid methy ester → 3-[1-(4-Chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethyl propanol

HRID 1090199Notes

Reaction equation

HRID 1090199 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:27])([CH3:26])[CH2:5][C:6]1[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:8]2[C:13]([C:14]=1[CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][CH:9]=2.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:7]2[C:8]3[C:13](=[CH:12][C:11]([O:16][CH3:17])=[CH:10][CH:9]=3)[C:14]([CH3:15])=[C:6]2[CH2:5][C:4]([CH3:27])([CH3:26])[CH2:3][OH:2])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 156787923-[1-(4-Chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethyl propanoic acid methy esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 156787933-[1-(4-Chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethyl propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

700 mg of 3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethyl propanoic acid methy ester was dissolved in 20 ml dry tetrahydrofuran. The reaction was cooled to -78° C. and 2 equivalents di-isobutyl aluminium hydride (DIBAL) in THF was added. The reaction was allowed to warm to room temperature and quenched with NH4Cl (aq.). Ethyl acetate was added (75 ml) and the organic phase separated, dried and evaporated. The product was isolated by column chromatography.

Workup

  1. temperatureto warm to room temperature
  2. customquenched with NH4Cl (aq.)
  3. additionEthyl acetate was added (75 ml)
  4. customthe organic phase separated
  5. customdried
  6. customevaporated
  7. customThe product was isolated by column chromatography

Sources & evidence

ORD record
ord-e4adbb1eb6bf4c04928b839c7741b7c7
Source dataset
uspto-grants-1992_01
Patent number
US05081145

Reaction notes

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