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

HRID 252062ノート

反応式

HRID 252062 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 57672260Tert-butyl 4-fluorocyclohexanecarboxylate収率 25%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7cafb82b456f4976942f2acfdee2b7b2
出典データセット
uspto-grants-2011_01
特許番号
US07868008B2

反応ノート

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