Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → HCID 86703787, compound

HRID 1849909Notes

Reaction equation

HRID 1849909 reaction equation
[C:1]12([CH2:11][OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Cl:13][C:14]1[C:15]([F:25])=[C:16]([CH:20]=[C:21]([F:24])[C:22]=1F)[C:17]([OH:19])=[O:18].CC(C)([O-])C.[K+]>CS(C)=O.CCOC(C)=O>[C:1]12([CH2:11][O:12][C:22]3[C:21]([F:24])=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[C:15]([F:25])[C:14]=3[Cl:13])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 3

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 27342693-Chloro-2,4,5-trifluorobenzoic AcidHCID 23665647Potassium tert-butoxide

Product 1

HCID 86703787HCID 86703787, compoundYield 150.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-adamantylmethanol (309 mg) and 3-chloro-2,4,5-trifluoro-benzoic acid (391 mg) in DMSO (5.6 mL) at 14° C. (bath) was added potassium tert-butoxide (458 mg) gradually. The mixture was stirred at that temp for 30 min. Diluted with EtOAc, the contents were washed with 1:4 mixture of 1M HCl and 1M NaH2PO4 (3×) and brine, and dried (Na2SO4). After filtration and concentration, the product was obtained as white solid (1.00 g).

Workup

  1. washthe contents were washed with 1:4 mixture of 1M HCl and 1M NaH2PO4 (3×) and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-5a387b35ca1d4794983365036a22f768
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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