Potassium Carbonate → 4-(3-Butyn-1-yl)benzenemethanol

HRID 1916533Notes

Reaction equation

HRID 1916533 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]=O)=[CH:11][CH:10]=1.[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO.CCOC(C)=O>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][OH:7])=[CH:10][CH:11]=1)[CH2:16][C:17]#[CH:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 534252763-(4-(Hydroxymethyl)phenyl)propanalHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 235966094-(3-Butyn-1-yl)benzenemethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

8.5 g (61.5 mmol) K2CO3 are added to a solution of 5.0 g (30.4 mmol) 3-(4-hydroxymethyl-phenyl)-propionaldehyde in 100 mL MeOH and then a solution of 7.0 g (36.4 mmol) dimethyl (1-diazo-2-oxo-propyl)-phosphonate in 50 mL MeOH is added dropwise and stirred for 3 h at RT. The reaction mixture is diluted with 200 mL EtOAc, washed with 80 mL saturated NaHCO3 solution, the aqueous phase extracted with 100 mL EtOAc and the combined organic phases are dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography on silica gel (cyc/EtOAc 3:1).

Workup

  1. washwashed with 80 mL saturated NaHCO3 solution
  2. extractionthe aqueous phase extracted with 100 mL EtOAc
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. customis purified by chromatography on silica gel (cyc/EtOAc 3:1)

Sources & evidence

ORD record
ord-c2b8312956604758a7c076246942cb16
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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