1-Bromopropane → HCID 15078285, compound

HRID 1110834Notes

Reaction equation

HRID 1110834 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 x) 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 x) 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-f28f8c320e504be5b69c1a986419addd
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

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