Diethyl Ether → 1-(3,5,5-Trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

HRID 1665940ノート

反応式

HRID 1665940 の反応式
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[C:4]2[CH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:3]=12.[CH2:16](OCC)C>C[Li]>[CH3:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:16])=[C:4]2[CH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:3]=12

参加物

4

反応物 2

HCID 3283Diethyl EtherHCID 57508884HCID 57508884、化合物

生成物 1

HCID 574374241-(3,5,5-Trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

試薬・触媒・溶媒 1

HCID 178418348HCID 178418348、化合物溶媒

反応条件

温度
26 °C

実験手順

To a suspension of 3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (4.10 g, 18.28 mmol) in diethyl ether (300 mL), methyllithium (23 mL, 1.6 M solution in diethyl ether) is slowly added at rt. The reaction mixture becomes clear, yellow and slightly warm (26° C.), and is stirred for 15 min before it is quenched with water. The organic layer is separated, washed once more with water, dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (2.80 g) as a pale yellow crystalline solid; LC-MS: tR=1.06 min, [M+1]=223.17; 1H NMR (CDCl3): δ 3.00 (t, J=7.0 Hz, 2H), 2.43 (s, 3H), 2.31 (s, 3H), 2.26 (s, 2H), 1.51 (t, J=7.0 Hz, 2H), 0.95 (s, 6H).

後処理

  1. additionis slowly added at rt
  2. customis quenched with water
  3. customThe organic layer is separated
  4. washwashed once more with water
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

出典と根拠

ORDレコード
ord-997e90611c4c4ca5aaf3c0df0dc75358
出典データセット
uspto-grants-2011_10
特許番号
US08039644B2

反応ノート

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