Diethyl Ether → HCID 23039569, compound

HRID 1284199Notes

Reaction equation

HRID 1284199 reaction equation
CCOCC.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[Mg].[CH:16]1([C:19](=[O:25])[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]1>O>[BrH:6].[CH:16]1([C:19]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)([OH:25])[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 3283Diethyl Ether3×HCID 77304-BromoanisoleHCID 2319851-cyclopropyl-3-(dimethylamino)propan-1-oneHCID 5462224Magnesium

Product 1

HCID 23039569HCID 23039569, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The stirred ether solution of the Grignard reagent prepared from 86 g. (0.46 mole) of 4-bromoanisole and 11.2 g. (0.46 mole) of magnesium in 200 ml. of dry ether was treated dropwise with a solution of 30 g. (0.23 mole) of 1-cyclopropyl-3-dimethylamino-1-propanone in 100 ml. of dry ether. After addition the mixture was allowed to warm to room temperature and was then hydrolyzed with water. The mixture was worked up as in Example 1 to give 16 g. (28%) of an oil which distilled at 110°-115°C./0.10 mm. The hydrobromide salt melted at 175°-177°C.

Workup

  1. additionAfter addition the mixture
  2. customto give 16 g
  3. distillation(28%) of an oil which distilled at 110°-115°C./0.10 mm

Sources & evidence

ORD record
ord-2b970065005f4995833487e9bf17442b
Source dataset
uspto-grants-1976_08
Patent number
US03978130

Reaction notes

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