Sodium hydride → HCID 22504538, compound

HRID 1368936Notes

Reaction equation

HRID 1368936 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[C:11](/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)\[CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1.[O:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39]Cl.[Cl-].[NH4+]>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:39][CH2:38][O:37][CH2:36][CH2:35][O:34][CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][O:28]3)=[CH:25][CH:26]=2)=[C:11](/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)\[CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 109657372-[2-(2-Chloroethoxy)ethoxy]oxaneHCID 22504517HCID 22504517, compound

Product 1

HCID 22504538HCID 22504538, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

NaH (0.09 g, 2.69 mmol) is mixed with dimethylformamide (DMF) (30 ml). (E)-4-(4-Chlorophenyl)-4-(4-hydroxyphenyl)-3-phenylbut-3-en-1-ol is dissolved in the solution and the mixture is heated to 60° C. and stirred for half an hour. 2-[(2-(Tetrahydropyranyloxy)ethoxy]ethyl chloride (0.83 g, 4.03 mmol) dissolved in DMF (5 ml) is added to the solution and heating is continued for 3 hours. Saturated aqueous ammonium chloride solution (30 ml) and toluene (30 ml) is added to the cooled reaction mixture and stirring is continued for 10 minutes. Layers are separated and aqueous layer is extracted with toluene (30 ml). Toluene phases are combined and washed with 2 N aqueous sodium hydroxide and three times with water. Organic phase is dried and evaporated to dryness. Yield 1.4 g, 99%.

Workup

  1. additionis added to the solution
  2. temperatureheating
  3. stirringstirring
  4. waitis continued for 10 minutes
  5. customLayers are separated
  6. extractionaqueous layer is extracted with toluene (30 ml)
  7. washwashed with 2 N aqueous sodium hydroxide and three times with water
  8. customOrganic phase is dried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-fde5a45daf1b4b5f8f1472d58c8698d5
Source dataset
uspto-grants-2003_06
Patent number
US06576645B1

Reaction notes

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