4,4-diphenyl-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]phosphepinium bromide → HCID 15789221, compound

HRID 2398Notes

Reaction equation

HRID 2398 reaction equation
[Br-].[C:2]1([P+:8]2([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:14][C:13]3[CH:15]=[CH:16][C:17]4[C:22]([C:12]=3[C:11]3[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=5[CH:29]=[CH:30][C:10]=3[CH2:9]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1(C)C=CC=CC=1>[C:2]1([P:8]([CH2:9][C:10]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:11]=2[C:12]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:13]=2[CH3:14])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 110060894,4-diphenyl-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]phosphepinium bromideHCID 21226445Aluminium lithium hydride

Product 1

HCID 15789221HCID 15789221, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4 g (7.3 mmol) of 4,4-diphenyl-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]phosphepinium bromide are suspended under a protective gas in 70 ml of absolute toluene. 500 mg (14.3 mmol) of lithium aluminum hydride are added to this suspension and the reaction solution is heated to boiling for 5 hours. Unreacted lithium aluminum hydride is subsequently filtered off. The organic phase is extracted with 20 ml of 1N sodium hydroxide solution and subsequently with 20 ml portions of water until the aqueous phase has a pH of from 6 to 7. The organic phase is dried over sodium sulfate and the toluene is drawn off at 12 torr/40° C. The wax-like residue is admixed with 15 ml of oxygen-free isopropanol, boiled and crystallized.

Workup

  1. temperaturethe reaction solution is heated
  2. filtrationUnreacted lithium aluminum hydride is subsequently filtered off
  3. extractionThe organic phase is extracted with 20 ml of 1N sodium hydroxide solution and subsequently with 20 ml portions of water until the aqueous phase
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customis drawn off at 12 torr/40° C
  6. customcrystallized

Sources & evidence

ORD record
ord-baa38a8e99a645bba8da7e83b29c024a
Source dataset
uspto-grants-1998_03
Patent number
US05728886

Reaction notes

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