Triethylamine → HCID 9863466, compound

HRID 977227Notes

Reaction equation

HRID 977227 reaction equation
FC(S(O[C:9]1[CH2:14][CH2:13][C:12]([C:29]#[N:30])([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:16]=2)[CH2:11][CH:10]=1)(=O)=O)(F)F.C(N(CC)CC)C.[CH3:38][OH:39].CN(C)[CH:42]=[O:43]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:29]([C:12]1([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:16]=2)[CH2:13][CH2:14][C:9]([C:38]([O:43][CH3:42])=[O:39])=[CH:10][CH2:11]1)#[N:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9889714HCID 9889714, compoundHCID 21901440N,N-dimethylformamide methanol

Product 1

HCID 9863466HCID 9863466, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-cyclohexenyl trifluoromethylsulfonate (1.0 g, 2.24 mmol) in 1:1 methanol/N,N-dimethylformamide (8 mL) were added triethylamine (0.66 mL, 4.72 mmol) and tetrakis(triphenylphosphine)palladium (0.13 g, 0.11 mmol). The resulting mixture was stirred at room temperature in the dark under a carbon monoxide atmosphere for 3 h. The mixture was partitioned between water and ethyl acetate, the organic extract was washed three times with water, once with brine, was dried (potassium carbonate) and was evaporated. Purification by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, provided an off-white solid (0.64 g, 80%): m.p. 128°-129° C.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. extractionthe organic extract
  3. washwas washed three times with water
  4. dry with materialonce with brine, was dried (potassium carbonate)
  5. customwas evaporated
  6. customPurification by flash chromatography
  7. washeluting with 3:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-37c633bfc0e24306b87a5eb56e0f0735
Source dataset
uspto-grants-1997_03
Patent number
US05614540

Reaction notes

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