Methanol → HCID 58760708, compound

HRID 857361Notes

Reaction equation

HRID 857361 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:13][C:14]([O:17]C)=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.B(Br)(Br)Br.C(Cl)Cl.CO.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:13][C:14]([OH:17])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 131726142HCID 131726142, compound

Product 1

HCID 58760708HCID 58760708, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the methyl ether from Step 1 (0.35 g, 1.03 mmol) in CH2Cl2 (5 mL) at 0° C. was added 1M BBr3/CH2Cl2 (5.2 mL, 5.2 mmol) over a period of 55 minutes. The dark gummy suspension was then brought to RT for 2.5 hours. MeOH (≈5 mL) was then added at −78° C. followed by saturated NaHCO3 solution. The cold bath was removed and the mixture was stirred for 30 minutes. The product was then extracted with CH2Cl2 and the organic phase was washed with H2O. After drying (MgSO4), filtering, and evaporating, the residue was purified by flash chromatography (1:2, 1:1 EtOAc:hexane) to give a light brown solid (0.19 g).

Workup

  1. customThe cold bath was removed
  2. extractionThe product was then extracted with CH2Cl2
  3. washthe organic phase was washed with H2O
  4. dry with materialAfter drying (MgSO4)
  5. filtrationfiltering
  6. customevaporating
  7. customthe residue was purified by flash chromatography (1:2, 1:1 EtOAc:hexane)

Sources & evidence

ORD record
ord-6684fa99d35945919cadc3190eeab46b
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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