2-Methyl-3-butyn-2-ol → 4-(4-Carbo-tert.-butoxyphenyl)-2-methyl-3-butyn-2-ol

HRID 974213Notes

Reaction equation

HRID 974213 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]([OH:20])([C:18]#[CH:19])[CH3:17]>C(#N)C.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:19]#[C:18][C:16]([CH3:17])([OH:20])[CH3:15])=[CH:9][CH:8]=1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:14]

Participants

6

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 11334366Tert-butyl 4-bromobenzoate

Product 1

HCID 199856624-(4-Carbo-tert.-butoxyphenyl)-2-methyl-3-butyn-2-olYield 71.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

257.1 g of 4-Bromobenzoic acid tert.-butyl ester, 168 g of 2-methyl-3-butyn-2-ol and 15.6 g of (Ph3P)2PdCl2 in 1.5 l of absolute acetonitrile and 480 ml of triethylamine are stirred together at reflux for 6 hours under nitrogen. The product is then concentrated by evaporation and worked up with toluene/H2O to yield 185 g of an oil which slowly crystallises.

Workup

  1. temperatureat reflux for 6 hours under nitrogen
  2. concentrationThe product is then concentrated by evaporation

Sources & evidence

ORD record
ord-344a1f5b8d1045fc87c14d5deebee8c8
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

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