Diisobutylaluminumhydride → 9-(3',5'-Bistrifluoromethylbenzyloxy)nona-2-en-1-ol

HRID 373206

反応式

HRID 373206 の反応式
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][C:16](OCC)=[O:17].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1.ClCCl>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:25])([F:27])[F:26])[CH:23]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][CH2:16][OH:17]

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 54133067Ethyl 9-(3',5'-bistrifluoromethylbenzyloxy)nona-2-enoate

生成物 1

HCID 541435229-(3',5'-Bistrifluoromethylbenzyloxy)nona-2-en-1-ol収率 85.1%

試薬・触媒・溶媒 1

HCID 21877217Toluene methylene chloride溶媒

実験手順

7-(3',5'-bistrifluoromethylbenzyloxy)heptan-1-al (See Example 2, 4.97g, 13.96 mmol) was reacted with carboethoxymethylene triphenylphosphorane (4.86g, 13.96 mmol, Lancaster Synthesis Ltd., U.K.) in dry dichloromethane to give ethyl 9-(3',5'-bistrifluoromethylbenzyloxy)nona-2- enoate (5g). The ester (5g, 13.55 mmol) was reacted with diisobutylaluminium hydride (27 mmol) in toluene-dichloromethane at -30°. After conventional work-up, 9-(3',5'-bistrifluoromethylbenzyloxy)nona-2-en-1-ol (4.43g) was obtained. The alcohol was converted into 9-(3',5'-bistrifluoromethylbenzyloxy)nona-2-en-al by Swern oxidation (oxalyl chloride-dimethylsulphoxide, see EP-A-164 187).

出典と根拠

ORDレコード
ord-e2e70361501e4fbabea613fdc2d41a7a
出典データセット
uspto-grants-1992_11
特許番号
US05162367

関連ノート

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