Diisobutylaluminum hydride → {1-[3-(4-Trifluoromethoxy-phenyl)-prop-2-ynyl]-cyclobutyl}-methanol

HRID 852415Notes

Reaction equation

C([O:3][C:4]([C:6]1([CH2:10][C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=O)C.CC(C[AlH]CC(C)C)C>>[F:21][C:20]([F:22])([F:23])[O:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]#[C:11][CH2:10][C:6]2([CH2:4][OH:3])[CH2:7][CH2:8][CH2:9]2)=[CH:18][CH:17]=1

Participants

Reactant 2

HCID 14487Diisobutylaluminum hydride

HCID 694589361-[3-(4-Trifluoromethoxy-phenyl)-prop-2-ynyl]-cyclobutanecarboxylic acid ethyl ester

Product 1

HCID 69458280{1-[3-(4-Trifluoromethoxy-phenyl)-prop-2-ynyl]-cyclobutyl}-methanol

Procedure

In analogy to the procedure described in example 31E], reduction of 1-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-cyclobutanecarboxylic acid ethyl ester with 3 equivalent of DIBAL-H (1.2 M solution in toluene) gave the title compound as yellow oil.

Sources & evidence

ORD record: ord-7cadb8b8acd44bf8b0cfdfdcdff4f6bd
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253192B2

Reaction notes

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