Diethyl Ether → HCID 19816157, compound

HRID 1284189Notes

Reaction equation

HRID 1284189 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Mg].CCOCC.[CH3:16][N:17]([CH3:25])[CH2:18][CH2:19][C:20]([CH:22]1[CH2:24][CH2:23]1)=[O:21]>O>[CH:22]1([C:20]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)([OH:21])[CH2:19][CH2:18][N:17]([CH3:25])[CH3:16])[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 77304-BromoanisoleHCID 2319851-cyclopropyl-3-(dimethylamino)propan-1-oneHCID 5462224Magnesium

Product 1

HCID 19816157HCID 19816157, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The Grignard reagent prepared from 86 g. (0.46 mole) of 4-bromoanisole and 11.2 g. (0.46 mole) of magnesium metal in 200 ml. of dry ether was cooled to -20°C. and treated dropwise with 30 g. (0.23 mole) of cyclopropyl 2-dimethylaminoethyl ketone in 100 ml. of dry ether. After addition the mixture was allowed to warm to room temperature, then hydrolyzed with water and worked up as described in Preparation I. The oily product was distilled at 110°-115°C./0.1 mm.; the yield of free base was 16 g. (28%).

Workup

  1. additiontreated dropwise with 30 g
  2. additionAfter addition the mixture
  3. customas described in Preparation I
  4. distillationThe oily product was distilled at 110°-115°C./0.1 mm

Sources & evidence

ORD record
ord-5fe0fa7c8ee0438a8c1e9e6ae5b5e81b
Source dataset
uspto-grants-1976_08
Patent number
US03978129

Reaction notes

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