Cyclohexane, (bromomethyl)- → Methyl 3-cyclohexyl-2-methyl-2-phenylpropanate

HRID 494568

반응식

HRID 494568 반응식
[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].Br[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>O1CCCC1>[CH:25]1([CH2:24][C:4]([CH3:5])([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([O:2][CH3:1])=[O:12])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

참가 물질

5

반응물 3

HCID 137636Cyclohexane, (bromomethyl)-HCID 569653Methyl alpha-methylbenzeneacetateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 68874551Methyl 3-cyclohexyl-2-methyl-2-phenylpropanate수율 84.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A solution of 2-phenyl-propionic acid methyl ester (3.0 g, 18.27 mmol) in tetrahydrofuran (25 mL) at −78° C. was treated dropwise with the lithium hexamethyldisilazide (21.9 mL, 1M in tetrahydrofuran, 21.9 mmol) and stirred for 1 hour. Bromomethyl-cyclohexane (3.09 mL, 21.92 mmol) was added to the reaction and the reaction was allowed to warm to 25° C. and stirred for 18 hours. The solvent was removed in vacuo and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the ethyl acetate layers were combined, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane, then 2.5% ethyl acetate in hexane, and 5% ethyl acetate in hexane to give the title compound (4.02 g, 84%). 1H NMR (300 MHz, CDCl3): δ ppm 1.11 (m, 10H) 1.55 (m, 4H) 1.80 (m, 1H) 2.04 (m, 1H) 3.64 (m, 3H) 7.29 (m, 5H).

후처리

  1. stirringstirred for 18 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel eluting with hexane

출처 및 근거

ORD 기록
ord-ddfb2fe1ac2648dd89fd37fd398aae52
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538105B2

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