2-Methyl-3-butyn-2-ol → HCID 54381551, compound

HRID 484565Notes

Reaction equation

HRID 484565 reaction equation
Cl[CH2:2][C:3](=[CH2:15])[CH2:4][C:5]#[C:6][C:7]([CH3:14])=[CH:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:12].[CH3:16][C:17]([OH:21])([C:19]#[CH:20])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[OH:21][C:17]([CH3:18])([CH3:16])[C:19]#[C:20][CH2:2][C:3](=[CH2:15])[CH2:4][C:5]#[C:6][C:7]([CH3:14])=[CH:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 11430Potassium CarbonateHCID 53762825HCID 53762825, compound

Product 1

HCID 54381551HCID 54381551, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 118 mg (0.52 mmole) of 10-chloromethyl-6-methyl-5,10-undecadien-7-yn-2-one (produced in accordance with Example III), 46 mg (0.55 mmole) of 2-methyl-3-butyn-2-ol (purchased from Aldrich Chemical Co., Milwaukee, Wis.), 125 mg (0.90 mmole) of anhydrous potassium carbonate, 12 mg (0.12 mmole) of cuprous chloride, and 13 mg (0.057 mmole) of benzyltriethylammonium chloride in 0.75 mL of acetonitrile (HPLC-grade, purchased from Aldrich Chemical Co., Milwaukee, Wis.) was stirred vigorously at room temperature for 25 hours, during which time the mixture was maintained under an atmosphere of nitrogen. Isolation of the product as described in the procedure of Example III afforded, after removal of the volatile organic solvents at reduced pressure, 109 mg (77% yield) of the named C-18 ketone. The proton NMR spectrum of this compound exhibited a singlet at δ1.50 [6H's, C(CH3)2 ], a singlet at δ1.77 (CH3 bonded to C-6), a singlet at δ2.12 (CH3C=O), and two singlets at δ2.97 and 3.04 (4H's, hydrogens bonded to C-11 and C-9).

Workup

  1. temperaturewas maintained under an atmosphere of nitrogen
  2. customafforded
  3. customafter removal of the volatile organic solvents at reduced pressure, 109 mg (77% yield) of the named C-18 ketone

Sources & evidence

ORD record
ord-c0a04f9a55c94925b064794eb12233db
Source dataset
uspto-grants-1993_07
Patent number
US05231232

Reaction notes

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