Triethylamine → HCID 15171918, compound

HRID 654516Notes

Reaction equation

HRID 654516 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]2[O:13][C:12]([C:15]#[CH:16])([CH3:14])[CH2:11][CH2:10][C:9]=2[C:17]=1[CH3:18])(=[O:3])[CH3:2].Br[C:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[S:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]2[O:13][C:12]([C:15]#[C:16][C:22]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[S:24][CH:23]=3)([CH3:14])[CH2:11][CH2:10][C:9]=2[C:17]=1[CH3:18])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 123250Benzo(b)thiophene, 3-bromo-HCID 14478582HCID 14478582, compound

Product 1

HCID 15171918HCID 15171918, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 0.544 g of rac-6-acetyloxy-2-ethynyl3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran, 0.64 g of 3-bromobenzothiophene, 90 mg of triphenylphosphine, 20 mg of cuprous iodide, 2 ml of triethylamine and 40 ml of dimethylformamide was stirred and degased by a stream of argon for minutes. Palladium acetate, 30 mg, was then added and the mixture was heated at 95° C. for 5 hours. The reaction mixture was partitioned between saturated sodium bicarbonate solution and toluene. The organic phase was washed with water, dried and evaporated. The residue was chromatographed over 50 g of silica gel using toluene for elution. The combined clean fractions were crystallized from hexane to give the title compound with m.p. 96°-99°.

Workup

  1. customdegased by a stream of argon for minutes
  2. additionPalladium acetate, 30 mg, was then added
  3. customThe reaction mixture was partitioned between saturated sodium bicarbonate solution and toluene
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed over 50 g of silica gel
  8. washfor elution
  9. customThe combined clean fractions were crystallized from hexane

Sources & evidence

ORD record
ord-25843b7d606b4615986c601f481d91a3
Source dataset
uspto-grants-1992_07
Patent number
US05132310

Reaction notes

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