Sodium Phosphate, Dibasic → HCID 11206499, compound

HRID 1791032Notes

Reaction equation

HRID 1791032 reaction equation
[CH2:1]=[C:2]1[CH2:8][CH:7](S(C2C=CC=CC=2)(=O)=O)[C:6]2[CH:18]=[C:19]([C:22](=[O:24])[CH3:23])[CH:20]=[CH:21][C:5]=2[O:4][CH2:3]1.P([O-])([O-])(O)=O.[Na+].[Na+].CO.O1CCCC1>[Na].[Hg].O>[CH2:1]=[C:2]1[CH2:8][CH2:7][C:6]2[CH:18]=[C:19]([CH:22]([OH:24])[CH3:23])[CH:20]=[CH:21][C:5]=2[O:4][CH2:3]1

Participants

6

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 11221558HCID 11221558, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 11206499HCID 11206499, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 962WaterSolvent

Procedure

3.14 mg (6.82 mmol) of 5% sodium amalgam are added portionwise at 0° C. to 389 mg (1.14 mmol) of 1-[3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-yl]ethanone, prepared according to example 13, and 648 mg (4.55 mmol) of sodium hydrogenphosphate in suspension in 50 ml of a 1/1 methanol/tetrahydrofuran binary mixture. The reaction medium is subsequently stirred at ambient temperature for 4 hours. After addition of water and of dichloromethane and filtering off the mercury, the phases are separated and the aqueous phase is extracted three times with dichloromethane. The combined organic phases are washed with a slightly acidic aqueous solution and then with brine. Purification on silica gel (ethyl acetate/heptane 30/70) makes it possible to obtain 188 mg of 1-(3-methylene-2,3,4,5-tetrahydro-1-benzoxepin-7-yl)ethanol as a mixture with its pinacol dimer.

Workup

  1. customprepared
  2. filtrationof dichloromethane and filtering off the mercury
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted three times with dichloromethane
  5. washThe combined organic phases are washed with a slightly acidic aqueous solution
  6. customPurification on silica gel (ethyl acetate/heptane 30/70)

Sources & evidence

ORD record
ord-55d0fc010eec4baeac9b7ff4dcfea9bf
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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