Dimethylformamide → Dibenzyl ether

HRID 1250205Notes

Reaction equation

HRID 1250205 reaction equation
[H-].[Na+].OC1C=C([C@]23CC4N=[C:21]5[C:26](=[CH:27]C=4C[C@H]2CN(C)CC3)[CH:25]=[CH:24][CH:23]=[CH:22]5)C=CC=1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CN(C=[O:41])C>>[CH2:29]([O:41][CH2:27][C:26]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 6604777HCID 6604777, compound

Product 1

HCID 7657Dibenzyl ether

Procedure

Sodium hydride (60%, 79.2 mg) and anhydrous DMF (1 ml) were added to a reactor. A solution of (4aR, 12aR)-4a-(3-hydroxyphenyl)-2-methyl-1,2,3,4,4a,5,12,12a-octahydro-quinolino[2, 3-g]isoquinoline (530 mg, 1.58 mmol) in anhydrous DMF (23 ml), and benzyl bromide (0.20 ml, 1.66 mmol) were added to the reactor, followed by stirring at room temperature for 1 hour. After reaction was completed, an aqueous saturated sodium bicarbonate solution (50 ml), distilled water (50 ml), and toluene (250 ml) were added to the reaction solution, followed by fractionation. The aqueous layer was extracted twice with toluene (150 ml), and the organic layers were together dried over sodium sulfate, filtered, and then concentrated to obtain 531 mg of benzyl ether compound. The thus-obtained compound was supplied to next reaction without purification.

Workup

  1. customAfter reaction
  2. distillationan aqueous saturated sodium bicarbonate solution (50 ml), distilled water (50 ml), and toluene (250 ml)
  3. additionwere added to the reaction solution
  4. extractionThe aqueous layer was extracted twice with toluene (150 ml)
  5. dry with materialthe organic layers were together dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6c8c1b26fa4a44039690565c515a504a
Source dataset
uspto-grants-2002_01
Patent number
US06337330B1

Reaction notes

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