Triethylamine → HCID 86713160, compound

HRID 918966Notes

Reaction equation

HRID 918966 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[F:12][C:13]([F:25])([F:24])[C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:25][C:13]([F:12])([F:24])[C:14]1[CH:15]=[CH:16][C:17]([S:20]([O:11][CH:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 27773994-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 86713160HCID 86713160, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-ol (82 mmol, 13.0 g) in CH2Cl2 (80 mL) at 0° C. was added 4-(trifluoromethyl)benzenesulfonyl chloride (90 mmol, 20.0 g), Et3N (123 mmol, 12.4 g) and DMAP (8.19 mmol, 1.0 g). The reaction mixture was stirred at 0° C. and then gradually warmed up to room temperature. After stirring overnight, the reaction mixture was washed with sat. NH4Cl (300 mL). The aq layer was separated and extracted with CH2Cl2 (3×300 mL). The organic layers were combined, dried over MgSO4 and concentrated. Chromatography on silica gel, eluting with EtOAc and hexane, provided the title compound.

Workup

  1. temperaturegradually warmed up to room temperature
  2. stirringAfter stirring overnight
  3. washthe reaction mixture was washed with sat. NH4Cl (300 mL)
  4. customThe aq layer was separated
  5. extractionextracted with CH2Cl2 (3×300 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. washChromatography on silica gel, eluting with EtOAc and hexane

Sources & evidence

ORD record
ord-b22ff85c182b4a3eaac8b46468dd3d69
Source dataset
uspto-grants-2016_03
Patent number
US09272987B2

Reaction notes

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