(Diethylamino)sulfur trifluoride → Tert-butyl 4-fluorocyclohexanecarboxylate

HRID 252062노트

반응식

HRID 252062 반응식
O[CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CCN(S(F)(F)[F:21])CC>ClCCl>[F:21][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 16064595trans-tert-Butyl 4-hydroxycyclohexanecarboxylate

생성물 1

HCID 57672260Tert-butyl 4-fluorocyclohexanecarboxylate수율 25%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of tert-butyl 4-hydroxycyclohexanecarboxylate (1500 mg, 7.45 mmol) in dichloromethane (anhydrous, 20 ml), DAST was (1571 mg, 22.4 mmol) added at 0° C. The resulting mixture was stirred at 0° C. for 3 hours. The mixture was diluted with dichloromethane, quenched with sodium bicarbonate. The organic layer was separated, the aqueous phase was extracted with EtOAc. The combined organic layer were washed with water, brine, dried with androus sodium sulphate. The product was purified (flash chromatography, 10 to 20% EtOAc/hexanes) and obtained as a 210 mg of yellow oil (25%). 1H NMR (300 MHz, CDCl3): δ 5.60-5.80 (m, 1H), 4.99-5.09 (m, 2H), 4.73 (d, 2H), 3.34 (br, 2H), 2.29-2.32 (m, 2H), 1.44-1.46 (m, 9H).

후처리

  1. additionadded at 0° C
  2. customquenched with sodium bicarbonate
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic layer were washed with water, brine
  6. dry with materialdried with androus sodium sulphate
  7. customThe product was purified (flash chromatography, 10 to 20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-7cafb82b456f4976942f2acfdee2b7b2
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868008B2

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