Hydrochloric Acid → Methyl 3-oxo-2,3-dihydro-1-benzoxepin-7-carboxylate

HRID 1791040Notes

Reaction equation

HRID 1791040 reaction equation
N12CCCN=C1CCCCC2.[O:12]=[C:13]1[CH2:19][CH:18](S(C2C=CC=CC=2)(=O)=O)[C:17]2[CH:29]=[C:30]([C:33]([O:35][CH3:36])=[O:34])[CH:31]=[CH:32][C:16]=2[O:15][CH2:14]1.O.Cl>ClCCl>[O:12]=[C:13]1[CH:19]=[CH:18][C:17]2[CH:29]=[C:30]([C:33]([O:35][CH3:36])=[O:34])[CH:31]=[CH:32][C:16]=2[O:15][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22042264HCID 22042264, compound

Product 1

HCID 11138567Methyl 3-oxo-2,3-dihydro-1-benzoxepin-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.084 ml (1.05 equivalents) of 1,8-diazabicyclo[5.4.0]undec-7-ene is added at ambient temperature to 217 mg (0.6 mmol) of methyl 3-oxo-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to example 2, in suspension in 20 ml of dichloromethane. From the addition of the base, the medium becomes translucent and slightly yellow. After addition of water and 1N hydrochloric acid, the phases are separated by settling and then the aqueous phase is extracted three times with dichloromethane. The combined organic phases are washed with a saturated sodium hydrogencarbonate solution and then with brine. After drying and then concentrating under vacuum, 90 mg (68%) of methyl 3-oxo-2,3-dihydro-1-benzoxepin-7-carboxylate are obtained in the form of a white solid; M.p.=89–93° C.

Workup

  1. customprepared
  2. additionFrom the addition of the base
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted three times with dichloromethane
  5. washThe combined organic phases are washed with a saturated sodium hydrogencarbonate solution
  6. customAfter drying
  7. concentrationconcentrating under vacuum, 90 mg (68%) of methyl 3-oxo-2,3-dihydro-1-benzoxepin-7-carboxylate
  8. customare obtained in the form of a white solid

Sources & evidence

ORD record
ord-eb8285bcd2b84ff3b1be95b859facf7a
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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