Dichloromethane → 3,3-Bis-(2-furanyl)-prop-2-en-1-ol

HRID 1247687Notes

Reaction equation

HRID 1247687 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)C.CC(C[AlH]CC(C)C)C.[Cl-].[NH4+].C(Cl)Cl>C1COCC1>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:6]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)=[CH:5][CH2:4][OH:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 122650993,3-Bis-(2-furanyl)-acrylic acid ethyl ester

Product 1

HCID 219077603,3-Bis-(2-furanyl)-prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,3-bis-(2-furanyl)-acrylic acid ethyl ester (1.31 g, 5.66mmol) in THF (15 ml) was added a solution of DIBAL-H (1 M in toluene, 25.5 ml, 25.5 mmol) at −10° C. The reaction mixture was stirred for a further 2 h. A solution of ammonium chloride (2 ml) was added followed by methylene chloride (250 ml) and decalite. The mixture was filtered and the filter was washed with additional methylene chloride (500 ml) and ethanol (100 ml). The combined organic phases were evaporated to give crude 3,3-bis-(2-furanyl)-prop-2-en-1-ol in 953 mg (88%) yield.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter was washed with additional methylene chloride (500 ml) and ethanol (100 ml)
  3. customThe combined organic phases were evaporated

Sources & evidence

ORD record
ord-96b5a95354a24e488a213975a217618a
Source dataset
uspto-grants-2006_10
Patent number
US07129268B2

Reaction notes

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