Potassium Carbonate → HCID 53905082, compound

HRID 484569Notes

Reaction equation

HRID 484569 reaction equation
Cl[CH2:2][C:3](=[CH2:10])[CH2:4][C:5]#[C:6][C:7]([CH3:9])=[CH2:8].[CH3:11][C:12]([C:19]#[CH:20])=[CH:13][CH2:14][CH2:15][C:16](=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[CH3:11][C:12]([C:19]#[C:20][CH2:9][C:7](=[CH2:8])[CH2:6][C:5]#[C:4][C:3]([CH3:10])=[CH2:2])=[CH:13][CH2:14][CH2:15][C:16](=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19748550HCID 19748550, compoundHCID 54188136HCID 54188136, compound

Product 1

HCID 53905082HCID 53905082, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Using a modification of the procedure suggested by T. Jeffery, Tetrahedron Lett., 30, 2225 (1989), a mixture of 175 mg (1.13 mmoles) of 6-chloromethyl-2-methyl-1,6-heptadien-3-yne (produced in accordance with Example XII), 139 mg (1.02 mmoles) of 6-methyl-5-octen-7-yn-2-one (produced in accordance with Example II), 220 mg (1.6 mmoles) of anhydrous potassium carbonate, 50 mg (0.50 mmole) of cuprous chloride, and 30 mg (0.13 mmole) of benzyltriethylammonium chloride in 1.00 mL of acetonitrile (HPLC-grade) was stirred vigorously at room temperature for 21 hours, during which time the mixture was maintained under a nitrogen atmosphere. Isolation of the product as described in the procedure of Example III afforded, after fractional evaporative distillation, 207 mg (80% yield) of the named unsaturated ketone: boiling point 122°-135° C. (bath temperature, 0.25 mm). The identity and purity of this compound were ascertained by highfield (300 MHz) proton NMR analysis. The proton NMR spectrum of the named ketone exhibited singlets at δ1.77 and 1.86 (two vinyl CH3 's), a singlet at δ2.12 (CH3C=O), a triplet (J=7.3Hz) at δ2.47 (CH2C=O), two singlets at δ3.08 and 3.09 (4H's, hydrogens bonded to C-9 and C-11), a singlet at δ5.15 (3 vinyl H's), a singlet at δ5.21 (one vinyl H), and a triplet at δ5.70 (vinyl hydrogen bonded to C-5).

Workup

  1. temperaturewas maintained under a nitrogen atmosphere
  2. customafforded

Sources & evidence

ORD record
ord-eed5f907abe94aa4be4f00ae7553909e
Source dataset
uspto-grants-1993_07
Patent number
US05231232

Reaction notes

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