Water → HCID 20145668, compound

HRID 648702Notes

Reaction equation

HRID 648702 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:17]([O:19][CH3:20])=[O:18])[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH2:7][C:6]1=[O:16].[BH4-].[Na+].O>CO>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:17]([O:19][CH3:20])=[O:18])[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH2:7][CH:6]1[OH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 20145672HCID 20145672, compound

Product 1

HCID 20145668HCID 20145668, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2.5 g of methyl 2-(3-chloropropyl)-3-oxo-3,4-dihydro-2H-1,5-benzodioxepin-2-carboxylate obtained in Reference Example 4 in 20 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, 1.75 g of methyl 2-(3-chloropropyl)-3-hydroxy-3,4-dihydro-2H-1,5-benzodioxepin-2-carboxylate (A isomer) is obtained as a colorless oil. Mass spectrum m/e: 300, 302 (M+). IR νmaxneat cm-1 : 3500(OH), 1755, 1735. NMR (CDCl3) δ: 3.21 (4H, multiplet), 3.3 (2H, triplet, ClCH2 --), 3.70 (3H, singlet, OCH3), 4.2 (3H, multiplet).

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-b47f487649024c5fbe47117bdb16bbf9
Source dataset
uspto-grants-1988_04
Patent number
US04736031

Reaction notes

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