Potassium Carbonate → (4-Ethynylphenyl)(4-fluorophenyl)methanol

HRID 710319Notes

Reaction equation

HRID 710319 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:17])[C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:18]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.C([O-])([O-])=O.[K+].[K+]>CO>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[OH:17])=[CH:10][CH:11]=1)#[CH:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113682014-((4-Fluorophenyl)(hydroxy)methyl)benzaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86661773(4-Ethynylphenyl)(4-fluorophenyl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of Step B (0.21 g, 0.91 mmol), dimethyl(1-diazo-2-oxopropyl)phosphonate (0.21 g, 1.1 mmol) and K2CO3 (0.152 g, 1.1 mmol) in anhydrous MeOH (5 ml) was stirred for overnight at room temperature. The solvent was distilled off and the residue was taken in EtOAc (50 ml), washed with H2O and dried over MgSO4 and filtered. The filtrate was evaporated under reduced pressure to give the crude product (0.195 g; 95%), which was used in the next step without purification. 1H-NMR (CDCl3) 3.05 (s, 1H); 5.76 (s, 1H); 7.0 (tr, 2H, J=8.58 Hz); 7.25-7.33 (m, 4H); 7.44 (d, 2H, J=8.29 Hz).

Workup

  1. distillationThe solvent was distilled off
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a1c6effe40c9421f94cf9a89ddf8ff8d
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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