1-Bromopropane → HCID 15078285, compound

HRID 1196710Notes

Reaction equation

HRID 1196710 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[OH:5][CH2:6][CH2:7][S:8]([C:11]1[CH:12]=[C:13]([C:26](=[O:43])[CH2:27][CH2:28][C:29]([C:31]2[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([O:41][CH3:42])[CH:32]=2)=[O:30])[CH:14]=[C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]=1[OH:17])(=[O:10])=[O:9].C(=O)([O-])[O-]>CN(C=O)C>[OH:5][CH2:6][CH2:7][S:8]([C:11]1[CH:12]=[C:13]([C:26](=[O:43])[CH2:27][CH2:28][C:29]([C:31]2[CH:32]=[C:33]([O:41][CH3:42])[C:34]([O:39][CH3:40])=[C:35]([O:37][CH3:38])[CH:36]=2)=[O:30])[CH:14]=[C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]=1[O:17][CH2:1][CH2:2][CH3:3])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 19660Carbonate IonHCID 15078284HCID 15078284, compound

Product 1

HCID 15078285HCID 15078285, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

n-Propyl bromide (1.63 mL, 17.8 mmol) was added to a solution of 1-[3-(2-hydroxyethylsulfonyl)-4-hydroxy-5-benzyloxyphenyl]-4-(3,4,5-trimethoxyphenyl)butan-1,4-dione (5.53 g, 9.91 mmol) in DMF (10 mL) containing postassium carbonate (2.74 g, 19.9 mmol). The mixture was stirred at 75° C. for 2 h, and partitioned between ethyl ether and water. The aqueous layer was re-extracted with ether (2 ×) and ethyl acetate. The organic extracts were combined, dried, and evaporated to dryness. The residue was triturated with Et2O to give crystals, which was washed with Et2O containing a small volume of acetone. This material, Rf 0.53 (hexane-ethyl acetate; 1:2, v/v), was used directly in the next experiment without further purification.

Workup

  1. custompartitioned between ethyl ether and water
  2. extractionThe aqueous layer was re-extracted with ether (2 ×) and ethyl acetate
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was triturated with Et2O
  6. customto give crystals, which
  7. washwas washed with Et2O containing a small volume of acetone
  8. custom1:2, v/v), was used directly in the next experiment without further purification

Sources & evidence

ORD record
ord-bc0c636fc99d44049738a41aaba32eba
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

Loading…