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

HRID 1916533

反応式

HRID 1916533 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c2b8312956604758a7c076246942cb16
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

関連ノート

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