Dichloromethane → (e)-3-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-3-phenylprop-2-en-1-ol

HRID 1039519Notes

Reaction equation

HRID 1039519 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14](=O)/[CH:15]=[C:16](/[C:23]1[CH:28]=[CH:27][C:26]([C:29]#[C:30][CH2:31][N:32]([CH3:34])[CH3:33])=[CH:25][CH:24]=1)\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C.[Cl-].[NH4+].ClCCl>O1CCCC1>[CH3:34][N:32]([CH3:33])[CH2:31][C:30]#[C:29][C:26]1[CH:27]=[CH:28][C:23](/[C:16](/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:15]/[CH2:14][OH:13])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 67145970(E)-3-[4-(3-dimethylamino-prop-1-ynyl)-phenyl]-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 67145875(e)-3-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-3-phenylprop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of diisobutylaluminum hydride in tetrahydrofuran (6 ml) was added drop wise to a cooled (0° C.) solution of the above ester (0.600 g; 1.80 mmol) in dry tetrahydrofuran (50 ml). The reaction stirred at the temperature for 4 hours and then added saturated ammoniumchloride (30 ml). After stirring 30 min dichloromethane (150 ml) and hyflo super cell medium (15 g) were added. The mixture was stirred at ambient temperature 2 hours, filtered and evaporated in vacuo. The crude product was taken up in dichloromethane (150 ml) and washed with water (2×50 ml), dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo giving (E)-3-[4-(3-dimethylamino-prop-1-ynyl)-phenyl]-3-phenylprop-2-en-1-ol.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at ambient temperature 2 hours
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. washwashed with water (2×50 ml)
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customsubsequently evaporated in vacuo

Sources & evidence

ORD record
ord-59403edf035c487da9a2ab3a03cb4e90
Source dataset
uspto-grants-2013_10
Patent number
US08551993B2

Reaction notes

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