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

HRID 380507Notes

Reaction equation

HRID 380507 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-22f91d74bdc84ba6b1fc4c772e251f88
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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