Ethanol → HCID 53686665, compound

HRID 372556Notes

Reaction equation

HRID 372556 reaction equation
[BH4-].[Na+].Cl.[CH2:4]([NH:7][CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[C:10](=[O:19])[CH2:9]1)[CH:5]=[CH2:6].C(O)C.[OH-].[Na+]>O>[CH2:4]([NH:7][CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH:10]([OH:19])[CH2:9]1)[CH:5]=[CH2:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 131711105HCID 131711105, compound

Product 1

HCID 53686665HCID 53686665, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

7.3 g of sodium borohydride was added over 30 minutes at 15° C to a solution of 7.3 g of the product of Step A in 7 3 ml of ethanol and 7.3 ml of water and the mixture was stirred for an hour at 20° C. The mixture was made alkaline with concentrated sodium hydroxide and the ethanol was evaporated. Water was added thereto and the mixture was extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness to obtain 6.2 g of 7-allylamino-5ξ-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene.

Workup

  1. customthe ethanol was evaporated
  2. additionWater was added
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f3c7cedc3099432b9a0b00020ba93c40
Source dataset
uspto-grants-1978_05
Patent number
US04091115

Reaction notes

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