HCID 12010474, compound → 1-Benzoxepin-3(2H)-one

HRID 1791037Notes

Reaction equation

HRID 1791037 reaction equation
I([O-])(=O)(=O)=O.[Na+].OC[C:9]1([OH:20])[CH:15]=[CH:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[O:11][CH2:10]1>O1CCOCC1.O>[O:11]1[C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH:14]=[CH:15][C:9](=[O:20])[CH2:10]1

Participants

4

Reactant 2

HCID 12010474HCID 12010474, compoundHCID 23667635Sodium periodate

Product 1

HCID 112636571-Benzoxepin-3(2H)-oneYield 70%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

4×28.5 mg (0.55 mmol) of sodium periodate are added in four equal portions over 30 minutes to 106 mg (0.55 mmol) of 3-(hydroxymethyl)-2,3-dihydro-1-benzoxepin-3-ol, prepared according to example 24, in solution in 3 ml of a 3/7 dioxane/water mixture. After stirring at ambient temperature for 2 hours, the medium is filtered through celite and the solid is discarded. After the usual extracting and washing treatments, purification by chromatography on silica gel (dichloromethane) provides 61 mg (70%) of 1-benzoxepin-3(2H)-one; 1H NMR (300 MHz, CDCl3): 7.45–7.35 (m, 2H), 7.15–7.25 (m, 3H), 6.38 (d, J=8.7 Hz, 1H), 4.55 (s, 2H).

Workup

  1. customprepared
  2. filtrationthe medium is filtered through celite
  3. extractionAfter the usual extracting
  4. washwashing
  5. customtreatments, purification by chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-4aac08ded32d4d21886abfba29f677cd
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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