Methanol → HCID 86676533, compound

HRID 595344Notes

Reaction equation

HRID 595344 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([C:19](=[O:21])[CH3:20])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[Br-:24].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[Br:24][CH2:20][C:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:14]=1)=[O:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 23500184Tetra-n-butylammonium tribromide2×HCID 67450496HCID 67450496, compound

Product 1

HCID 86676533HCID 86676533, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-[3-({3-[(phenylmethyl)oxy]propyl}oxy)phenyl]ethanone (10.59 g) in tetrahydrofuran (50 mL) was added methanol (50 mL) and a solution of tetrabutylammonium tribromide (16 g) in tetrahydrofuran (50 mL). The reaction was stirred at ambient temperature for 45 min at which time tetrabutylammonium tribromide (0.89 g) was added, followed by further addition of 0.6 g. 10% aqueous sodium thiosulfate was added to the reaction and the mixture was concentrated in vacuo to a minimum volume. Ethyl acetate was added and the resultant organic solution was washed with aqueous sodium thiosulfate, saturated sodium bicarbonate and brine and concentrated to an oil to afford the title compound.

Workup

  1. additionwas added
  2. additionfollowed by further addition of 0.6 g
  3. concentrationthe mixture was concentrated in vacuo to a minimum volume
  4. additionEthyl acetate was added
  5. washthe resultant organic solution was washed with aqueous sodium thiosulfate, saturated sodium bicarbonate and brine
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-674e4e1f275a439d9df00e7a02375228
Source dataset
uspto-grants-2016_01
Patent number
US09243003B2

Reaction notes

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