Water → HCID 14127334, compound

HRID 648700Notes

Reaction equation

HRID 648700 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:17]([O:19][CH3:20])=[O:18])[C:11](=[O:12])[CH2:10][CH2:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[O:6]1.[BH4-].[Na+].O>CO>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:17]([O:19][CH3:20])=[O:18])[CH:11]([OH:12])[CH2:10][CH2:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[O:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 14127331HCID 14127331, compound

Product 1

HCID 14127334HCID 14127334, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2.0 g of methyl 2-(3-chloropropyl)-3-oxo-2,3,4,5-tetrahydro-1-benzoxepin-2-carboxylate obtained in Reference Example 1 in 30 ml of methanol, sodium borohydride is added in small portions with stirring and under ice-cooling. After completion of the reaction, the reaction mixture is treated with water and extracted with ethyl acetate. The organic layer is washed with water, dried, and evaporated under reduced pressure. The residue is purified by column chromatography on silica gel (eluant: hexane:ethyl acetate=3:1→1:1). From the first fraction eluted, methyl 2-(3-chloropropyl)-3-hydroxy-2,3,4,5-tetrahydro-1-benzoxepin-2-carboxylate (A isomer) is obtained as a colorless oil. Mass spectrum m/e: 298, 300 (M+). IR νmaxneat cm-1 : 3500 (OH), 1735. NMR(CDCl3) δ: 2.0 (6H, multiplet), 3.0(2H, multiplet), 3.5 (2H, triplet, ClCH2 --), 3.70 (3H, s, OCH3), 4.18 (1H, multiplet, C3 --H).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (eluant: hexane:ethyl acetate=3:1→1:1)
  8. washFrom the first fraction eluted

Sources & evidence

ORD record
ord-c71fa7b5b16b46ad8158abcfdf2f7574
Source dataset
uspto-grants-1988_04
Patent number
US04736031

Reaction notes

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