Triphenylphosphine → HCID 22664454, compound

HRID 1166591Notes

Reaction equation

HRID 1166591 reaction equation
Br[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:36][Si:37]([C:40]#[CH:41])([CH3:39])[CH3:38]>C(NC(C)C)(C)C>[CH3:36][Si:37]([C:40]#[C:41][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[CH:3]=1)([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 12437190HCID 12437190, compound

Product 1

HCID 22664454HCID 22664454, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 7912DiisopropylamineSolvent

Procedure

To a stirred mixture of 10-bromo-5H-dibenzo[a,d]cycloheptene (9.70 g, 0.036 mol) (J. Med. Chem. 1995 38(4), 708-714), palladium(II)chloride bistriphenylphosphine (1.25 g, 0.018 mol), triphenyl phosphine (0.942 g, 0.0036 mol), copper(ll)acetate hydrate (0.327 g, 0.002 mol) in 20 ml of diisopropyl amine was added (trimethylsilyl)acetylene (3.88 g, 0.040 mol) and refluxed for an hour. The resulting mixture was concentrated, diluted with hexane (25 ml) and filtered through a pad of silica gel. The filtrate was concentrated to yield 5.57 g of 10-(trimethylsilyl)ethynyl-5H-dibenzo[a,d]cycloheptene.

Workup

  1. temperaturerefluxed for an hour
  2. concentrationThe resulting mixture was concentrated
  3. additiondiluted with hexane (25 ml)
  4. filtrationfiltered through a pad of silica gel
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-667de43cd02246dea3b42869da0d12cf
Source dataset
uspto-grants-2003_09
Patent number
US06613921B2

Reaction notes

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