(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid → (1aS,5aR)-1-(1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone

HRID 1924818노트

반응식

HRID 1924818 반응식
[CH3:1][C:2]1([CH3:15])[C@@H:4]2[CH2:5][C:6]3[C:10]([C@H:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12]([OH:14])=O.[Li][CH3:17]>CCOCC>[CH3:15][C:2]1([CH3:1])[C@@H:4]2[CH2:5][C:6]3[C:10]([C@H:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12](=[O:14])[CH3:17]

참가 물질

4

반응물 2

HCID 57892448(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acidHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 59380608(1aS,5aR)-1-(1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone수율 74.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid (220 mg, 1.00 mmol) in Et2O (10 mL) is added a solution of MeLi (1.6 M, 1.4 mL, 2.10 mmol) in Et2O at such a pace that the reaction mixture is refluxing gently. Upon completion of the addition, stirring is continued at rt for 30 min. The reaction is quenched by adding sat. aq. NH4Cl (3 mL). The organic layer is separated, dried over Na2SO4 and the solvent is evaporated to give (1aS,5aR)-1-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone (165 mg) as a pale yellow oil; LC-MS: tR=1.03 min, [M+1]+=221.20; 1H NMR (CDCl3): δ 3.00 (ddd, J=1.8, 4.7, 18.8 Hz, 1H), 2.80 (d, J=18.8 Hz, 1H), 2.38 (s, 6H), 1.93-1.90 (m, 2H), 1.14 (s, 3H), 0.74 (s, 3H).

후처리

  1. temperatureis refluxing gently
  2. additionUpon completion of the addition
  3. customThe reaction is quenched
  4. additionby adding sat. aq. NH4Cl (3 mL)
  5. customThe organic layer is separated
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated

출처 및 근거

ORD 기록
ord-ddf37fcce97b4831837d79872724b8bc
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178562B2

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