Hydrochloric Acid → HCID 18319560, compound

HRID 1699372Notes

Reaction equation

HRID 1699372 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:19]2[O:18][CH2:17][CH2:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:2].[BH4-].[Na+].Cl>C(O)C.O1CCCC1>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:19]2[O:18][CH2:17][CH2:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18319566HCID 18319566, compound

Product 1

HCID 18319560HCID 18319560, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2,3-dihydro-9-(2-formylphenyl)-1-benzoxepin-4-carboxylate (0.58 g) in a mixture of ethanol (5.8 ml) and tetrahydrofuran (3 ml) was added sodium borohydride (34 mg) at 0 C. The reaction mixture was stirred for 30 minutes at ambient temperature, thereto was added 1N hydrochloric acid (2 ml), and evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated n vacuo. The residue was purified by medium pressure liquid chromatography (silica gel) using a mixture of ethyl acetate and n-hexane (1:9) as an eluent to give a solid of ethyl 2,3-dihydro-9-(2-hydroxymethylphenyl)-1-benzoxepin-4-carboxylate (530 mg).

Workup

  1. customevaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated n vacuo
  6. customThe residue was purified by medium pressure liquid chromatography (silica gel)
  7. additiona mixture of ethyl acetate and n-hexane (1:9) as an eluent

Sources & evidence

ORD record
ord-3a4f594335d246018b05e10d65883cc1
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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