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

HRID 252062Notes

Reaction equation

HRID 252062 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 57672260Tert-butyl 4-fluorocyclohexanecarboxylateYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-7cafb82b456f4976942f2acfdee2b7b2
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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