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

HRID 549907Notes

Reaction equation

HRID 549907 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 67145969(Z)-3-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 67145876(z)-3-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-3-phenyl-prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of diisobutylaluminum hydride in tetrahydrofuran (8 mL) was added drop wise to a cooled (0° C.) solution of the above ester (0.650 g; 1.80 mmol) in dry tetrahydrofuran (50 mL). The reaction stirred at the temperature for 3 hours and then added saturated ammonium chloride (30 ml). The resulting mixture was stirred for 30 min, and the mixture was then added dichloromethane (150 ml) and hyflo super cell medium (15 g). The resulting suspension was stirred at ambient temperature 2 hours. The mixture was filtered and subsequently evaporated in vacuo. The crude product were taken up in dichloromethane (150 ml) and washed with water (2×50 ml). The dichloromethane phase was dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo giving (Z)-3-[4-(3-dimethylamino-prop-1-ynyl)-phenyl]-3-phenyl-prop-2-en-1-ol

Workup

  1. stirringThe resulting mixture was stirred for 30 min
  2. stirringThe resulting suspension was stirred at ambient temperature 2 hours
  3. filtrationThe mixture was filtered
  4. customsubsequently evaporated in vacuo
  5. washwashed with water (2×50 ml)
  6. dry with materialThe dichloromethane phase was dried with anhydrous magnesium sulfate
  7. customsubsequently evaporated in vacuo

Sources & evidence

ORD record
ord-c591e2bdd6304d18817eebc0fc5c3ca0
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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