1-Butanol → 3'-isopropyl-3,4-dihydro-2H-1,5-benzodioxepin-3-spiro-5'-oxazolidin-2'-one

HRID 267779

Reaction equation

HRID 267779 reaction equation
[OH:1][C:2]1([CH2:13][NH:14][CH:15]([CH3:17])[CH3:16])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:3]1.[C:18](=O)(OCCCC)[O:19]CCCC.[Na].C(O)CCC>C1C=CC=CC=1>[CH:15]([N:14]1[CH2:13][C:2]2([CH2:8][O:7][C:6]3[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=3[O:4][CH2:3]2)[O:1][C:18]1=[O:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 68333Dibutyl carbonate2×HCID 5360545SodiumHCID 15557308HCID 15557308, compound

Product 1

HCID 155573263'-isopropyl-3,4-dihydro-2H-1,5-benzodioxepin-3-spiro-5'-oxazolidin-2'-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-hydroxy-3-isopropylaminomethyl-3,4-dihydro-2H-1,5-benzodioxepin (11.85 g.; 50 millimoles), prepared as described in Example 1, and dibutyl carbonate (13.1 g.) with a small piece of metallic sodium is heated in an oil bath. The temperature then is slowly raised to 170° C. with removal of butanol. Finally, the mixture is heated between 170°-200° C. with removal of excess dibutyl carbonate. The cooled reaction product is dissolved in benzene, washed with water, dried over sodium sulfate, and the solvent evaporated to give 3'-isopropyl-3,4-dihydro-2H-1,5-benzodioxepin-3-spiro-5'-oxazolidin-2'-one, m.p. 121°-122° C.

Workup

  1. customprepared
  2. temperatureis heated in an oil bath
  3. customThe cooled reaction product
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-baf10c7490ea425cbcdd0e469640b157
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Linked notes

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