1,4-Dibromobutane → HCID 15078314, compound

HRID 1196702Notes

Reaction equation

HRID 1196702 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[OH:7][CH:8]([CH3:41])[CH2:9][S:10]([C:13]1[CH:14]=[C:15]([C@H:24]2[CH2:28][CH2:27][C@H:26]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[O:25]2)[CH:16]=[C:17]([OH:23])[C:18]=1[O:19][CH2:20][CH2:21][CH3:22])(=[O:12])=[O:11].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:7][CH:8]([CH3:41])[CH2:9][S:10]([C:13]1[CH:14]=[C:15]([C@H:24]2[CH2:28][CH2:27][C@H:26]([C:29]3[CH:30]=[C:31]([O:39][CH3:40])[C:32]([O:37][CH3:38])=[C:33]([O:35][CH3:36])[CH:34]=3)[O:25]2)[CH:16]=[C:17]([O:23][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[C:18]=1[O:19][CH2:20][CH2:21][CH3:22])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 15078298HCID 15078298, compound

Product 1

HCID 15078314HCID 15078314, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1,4-Dibromobutane (75 uL, 0.63 mmol) was added to a solution of trans-2-[3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (75 mg, 0.15 mmol) in DMF (0.5 mL) containing potassium carbonate (75 mg, 0.54 mmol). The reaction mixture was heated with stirring under nitrogen at 70° C. for 1.5 h, cooled, and partitioned between ethyl ether and water. The ethereal layer was separated and the aqueous layer was re-extracted twice with ether. The organic extracts were combined, dried, and evaporated to a residue. Purification by preparative TLC (hexane-ethyl acetate; 1:1, v/v) gave the title compound as a colorless viscous oil: Rf 0.5; NMR (CDCl3) δ 1.25 (d, CH2CHOHCH3).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled
  3. custompartitioned between ethyl ether and water
  4. customThe ethereal layer was separated
  5. extractionthe aqueous layer was re-extracted twice with ether
  6. customdried
  7. customevaporated to a residue
  8. customPurification by preparative TLC (hexane-ethyl acetate

Sources & evidence

ORD record
ord-711efbe6272f4e50a96233846f631d73
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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