3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid → 1-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

HRID 1013441노트

반응식

HRID 1013441 반응식
[CH2:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12)[CH3:2].[CH3:17][Li]>C(OCC)C>[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:17])=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12)[CH3:2]

참가 물질

4

반응물 2

HCID 574374183-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acidHCID 178418348HCID 178418348, 화합물3회

생성물 1

HCID 574374251-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (2.10 g, 8.81 mmol) in diethyl ether (100 mL), a solution of methyllithium (11 mL, 1.6 M solution in diethyl ether) is added at rt. The pale yellow solution is stirred at rt for 15 min before another portion of methyllithium (2 mL) is added. Stirring is continued for 15 min, a further portion of methyllithium (1 mL) is added, and the mixture is again stirred for 15 min at rt. The reaction 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 7:3 to give 1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (1.65 g) as a pale yellow solid; LC-MS: tR=1.00 min; [M+1]=237.15; 1H NMR (CDCl3): δ 3.03 (t, J=7.0 Hz, 2H), 2.73 (q, J=7.6 Hz, 2H), 2.47 (s, 3H), 2.31 (s, 2H), 1.55 (t, J=7.0 Hz, 2H), 1.28 (t, J=7.6 Hz, 3H), 0.97 (s, 6H).

후처리

  1. additionis added
  2. stirringthe mixture is again stirred for 15 min at rt
  3. customThe reaction is quenched with water
  4. customThe organic layer is separated
  5. washwashed once more with water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe crude product is purified by CC on silica gel eluting with heptane:EA 7:3

출처 및 근거

ORD 기록
ord-5610634bf46c4e48980b1613aef5f9db
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981924B2

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