1-Bromohexane → HCID 53633266, compound

HRID 1779328Notes

Reaction equation

HRID 1779328 reaction equation
[CH3:1][O:2][P:3]([O:22][CH3:23])([C:5](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=1)[C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])=[O:4].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][P:3]([O:22][CH3:23])([C:5](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:14]=1)[C:6]([O:8][CH:9]([CH3:10])[CH3:11])=[O:7])=[O:4]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 53798304HCID 53798304, compound

Product 1

HCID 53633266HCID 53633266, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isopropyl 2-(dimethoxyphosphinyl)-3-(3-hydroxy-4-methoxy-phenyl)propenoate (2 g; 0.0058 mol; Table 1, No. 26), 1-bromohexane (0.85 ml; 0.006 mol), 30 ml of dimethylformamide (DMF) and potassium carbonate (ground, 0.89 g; 0.0065 mol) were mixed and stirred at room temperature for 6 hours. The filtrate after removal of the inorganic salts was evaporated under reduced pressure. Residues of DMF were removed from the resulting oily residue in a kugelrohr apparatus at 70° C./0.02 mm Hg, and it was then chromatographed on silica gel eluting with a dichioromethane:ethane acetate (8:2) mixture. This resulted in a pale oil. Yield: 3.6 g (72.5% of theory)

Workup

  1. customThe filtrate after removal of the inorganic salts
  2. customwas evaporated under reduced pressure
  3. customResidues of DMF were removed from the resulting oily residue in a kugelrohr apparatus at 70° C./0.02 mm Hg, and it
  4. customwas then chromatographed on silica gel eluting with a dichioromethane:ethane acetate (8:2) mixture
  5. customThis resulted in a pale oil

Sources & evidence

ORD record
ord-6934521e439141c69fe817b90fee2626
Source dataset
uspto-grants-1997_05
Patent number
US05627173

Reaction notes

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