Methyl chloroformate → 4-Fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate

HRID 471984

반응식

HRID 471984 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:3]=1.Cl[C:17]([O:19][CH3:20])=[O:18]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:17](=[O:18])([O:19][CH3:20])[O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[C:9]1([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

참가 물질

5

반응물 2

HCID 6586Methyl chloroformateHCID 593949974-Fluoro-2-(1-methylcyclohexyl)phenol

생성물 1

HCID 593950614-Fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate수율 72.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-fluoro-2-(1-methylcyclohexyl)phenol (23.5 g, 113 mmol), TEA (31 mL, 226 mmol) and DMAP (700 mg, 5.7 mmol) in CH2Cl2(250 mL) was added methyl chloroformate dropwise at 0° C. The mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was poured onto crushed ice and extracted with CH2Cl2(100 mL×3). The organic layer was washed with brine, dried over MgSO4, evaporated under vacuum. The crude product was purified by chromatography on silica gel diluted with (hexane:ethyl acetate=100:1) to give 4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate as red brown oil (43.9 g, 72.1% yield). 1H NMR (400 MHz, CDCl3) δ 7.10 (dd, J=3.2, 11.2 Hz, 1H), 7.05-7.02 (m, 1H), 6.93-6.88 (m, 1H), 3.91 (s, 3H), 2.02-1.96 (m, 2H), 1.66-1.36 (m, 8H), 1.23 (s, 3H).

후처리

  1. additionThe reaction mixture was poured
  2. customonto crushed ice
  3. extractionextracted with CH2Cl2(100 mL×3)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum
  7. customThe crude product was purified by chromatography on silica gel
  8. additiondiluted with (hexane:ethyl acetate=100:1)

출처 및 근거

ORD 기록
ord-e973f50cdbe84533bcdc80a070f89f6f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633189B2

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