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

HRID 1247684Notes

Reaction equation

HRID 1247684 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH3:18])[C:7]1[S:8][CH:9]=[CH:10][C:11]=1[CH3:12])C.CC(C[AlH]CC(C)C)C.[Cl-].[NH4+].C(Cl)Cl>C1COCC1>[CH3:12][C:11]1[CH:10]=[CH:9][S:8][C:7]=1[C:6]([C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH3:18])=[CH:5][CH2:4][OH:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 685759983,3-Bis-(3-methyl-thiophen-2-yl)-acrylic acid ethyl ester

Product 1

HCID 219076783,3-Bis-(3-methylthiophen-2-yl)-prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,3-bis-(3-methyl-thiophen-2-yl)-acrylic acid ethyl ester (2.12 g, 7.27 mmol) in THF (20 ml) was added a solution of DIBAL-H (1.5 M in toluene, 33 ml, 49.5 mmol) at −20° C. The reaction mixture was stirred for a further 2 h. A solution of ammonium chloride was added followed by methylene chloride (150 ml) and decalite. The mixture was filtered and the filter was washed with additional methylene chloride (500 ml). The combined organic phases were evaporated to give crude product. Purification on column chromatography gave 3,3-bis-(3-methyl-thiophen-2-yl)-prop-2-en-1-ol in 376 mg (21%) yield.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter was washed with additional methylene chloride (500 ml)
  3. customThe combined organic phases were evaporated
  4. customto give crude product
  5. customPurification on column chromatography

Sources & evidence

ORD record
ord-f597600d2491423e94ca3ce1f26f2e74
Source dataset
uspto-grants-2006_10
Patent number
US07129268B2

Reaction notes

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