Diisobutylaluminum hydride → (E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-prop-2-en-1-ol

HRID 403482Notes

Reaction equation

HRID 403482 reaction equation
C[O:2][C:3](=O)/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:14]([CH2:24][CH3:25])=[N:15][N:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18][C:17]=23)=[CH:8][CH:7]=1.CC(C[AlH]CC(C)C)C>ClCCl>[CH2:24]([C:14]1[C:13]([CH2:12][C:9]2[CH:8]=[CH:7][C:6](/[CH:5]=[CH:4]/[CH2:3][OH:2])=[CH:11][CH:10]=2)=[C:17]2[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]2[N:15]=1)[CH3:25]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 68379176(E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-acrylic acid methyl ester

Product 1

HCID 68378973(E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

(E)-3-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-acrylic acid methyl ester (4) (780 mg, 2.3 mmol), was dissolved in 23 ml dichloromethane and cooled to −78° C. A 1.2M solution of DIBAH in dichloromethane (5.8 ml, 7 mmol) was added dropwise.

Sources & evidence

ORD record
ord-9f7428c8bf324aa1bcb760fdeabc2fec
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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