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

HRID 380507

반응식

HRID 380507 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 15062252Methyl 2,3-dihydrobenzofuran-7-carboxylate수율 142.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-22f91d74bdc84ba6b1fc4c772e251f88
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303593B1

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