Hydrochloric Acid → 1-(4-Chloro-1-methyl-1-butenyl)-4-fluorobenzene

HRID 51009

反応式

HRID 51009 の反応式
[CH:1]1([C:4]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)(O)[CH3:5])[CH2:3][CH2:2]1.[ClH:14]>C(O)(C)C>[Cl:14][CH2:3][CH2:2]/[CH:1]=[C:4](/[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)\[CH3:5]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 981041-Cyclopropyl-1-(4-fluorophenyl)ethanol

生成物 1

HCID 63657691-(4-Chloro-1-methyl-1-butenyl)-4-fluorobenzene収率 84%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

1-Cyclopropyl-1-(4-fluorophenyl)ethanol (307 mg, 1.70 mmol) in a solution of 1 N HCl in isopropyl alcohol (3.6 mL) was heated at 60° C. for 1 h. The reaction mixture was then concentrated in vacuo, and column chromatography purification yielded 1-[(1E)-4-chloro-1-methyl-1-butenyl]-4-fluorobenzene (282 mg, 84%) as a colorless oil. The title compound was isolated as a yellow oil (36 mg, 70%) according to the method of Example 286, Step C from (8aS,12aR)-6,7,8a,9,10,11,12,12a-octahydro-5H-pyrido[4,3-b][1,4]thiazepino[2,3,4-hi]indole (30 mg, 0.12 mmol) and 1-[(1E)-4-chloro-1-methyl-1-butenyl]-4-fluorobenzene (48 mg, 0.24 mmol). 1H NMR (CDCl3) δ1.62 (br-s, 1H), 1.90-2.20 (m, 9H), 2.31-2.44 (m, 5H), 2.71-2.80 (m, 1H), 2.81-2.89 (m, 1H), 2.92-3.00 (m, 1H), 3.04-3.13 (m, 1H), 3.17-3.24 (m, 2H), 3.27-3.31 (m, 1H), 3.51-3.63 (m, 1H), 3.80-3.91 (m, 1H), 5.64-5.73 (m, 1H), 6.62 (t, 1H, J=7.5 Hz), 6.87 (d, 1H, J=6.6 Hz), 6.91-7.00 (m, 3H), 7.29-7.34 (m, 2H) ppm)

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo, and column chromatography purification

出典と根拠

ORDレコード
ord-76499072d7b74fada5138abaa5845af9
出典データセット
uspto-grants-2004_03
特許番号
US06713471B1

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