(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 86690089, compound

HRID 520367Notes

Reaction equation

HRID 520367 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[F:14][C:15]1([F:28])[CH2:20][CH2:19][C:18]([CH2:26]O)([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]1>>[F:14][C:15]1([F:28])[CH2:20][CH2:19][C:18]([CH2:26][F:11])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58815088HCID 58815088, compound

Product 1

HCID 86690089HCID 86690089, compound

Conditions

Temperature
70 °C

Procedure

A neat stirred mixture of Deoxo-Fluor® (196 mg, 0.887 mmol) and ethyl 4,4-difluoro-1-(hydroxymethyl)cyclohexanecarboxylate (98.6 mg, 0.444 mmol) was heated at 70° C. overnight. The reaction was cooled to rt and quenched with ice and extracted with DCM, washed with satd. NaHCO3, water, brine and dried (MgSO4). Evaporation of DCM gave a light brown oil which was purified by silica gel FCC (1:3 hexanes:DCM) to afford ethyl 4,4-difluoro-1-(fluoromethyl)cyclohexanecarboxylate as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 4.42 (d, J=47.2 Hz, 2H), 4.25 (q, J=7.0 Hz, 2H), 2.33-2.19 (m, 2H), 2.15-2.01 (m, 2H), 2.01-1.81 (m, 2H), 1.69-1.56 (m, 2H), 1.31 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled to rt
  2. customquenched with ice
  3. extractionextracted with DCM
  4. washwashed with satd
  5. dry with materialNaHCO3, water, brine and dried (MgSO4)
  6. customEvaporation of DCM
  7. customgave a light brown oil which
  8. customwas purified by silica gel FCC (1:3 hexanes:DCM)

Sources & evidence

ORD record
ord-09273b788846452588699cd985f3bcc5
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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