Benzyl Alcohol → Methyl 2,3-dihydrobenzofuran-7-carboxylate

HRID 380507ノート

反応式

HRID 380507 の反応式
[O:1]1[C:5]2[C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[CH2:13](O)C1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:10]([C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)([O:12][CH3:13])=[O:11]

参加物

6

反応物 3

HCID 244Benzyl AlcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acid

生成物 1

HCID 15062252Methyl 2,3-dihydrobenzofuran-7-carboxylate収率 142.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 0.2 g (1.22 mmol) of 7-dihydrobenzofuran carboxylic acid, 0.13 g (1.22 mmol) of benzyl alcohol, 0.3 g (2.44 mmol) of DMAP and 0.46 g (2.44 mmol) of 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride in 5 mL of CH2Cl2 was stirred at rt for 12 h. The reaction mixture was partitioned between CH2Cl2 and water and the pH was adjusted to pH=1 with 1N HCl solution. The reaction mixture was extracted with CH2Cl2 and the combined organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 6:1) to give 0.31 g of the title compound.

後処理

  1. customThe reaction mixture was partitioned between CH2Cl2 and water
  2. extractionThe reaction mixture was extracted with CH2Cl2
  3. dry with materialthe combined organic fraction was dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes: ethyl acetate, 6:1)

出典と根拠

ORDレコード
ord-22f91d74bdc84ba6b1fc4c772e251f88
出典データセット
uspto-grants-2001_10
特許番号
US06303593B1

反応ノート

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