Sodium Thiosulfate → Octahydro-3H-2-benzopyran-3-one

HRID 2371761Notes

Reaction equation

HRID 2371761 reaction equation
[CH2:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][C:2]1=[O:10].C([O-])(O)=[O:12].[Na+].ClC1C=CC=CC=1C(OO)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[CH2:1]1[CH:9]2[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]2[CH2:3][C:2](=[O:10])[O:12]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 138565Octahydro-2H-inden-2-oneHCID 516892Sodium BicarbonateHCID 125873982-Chlorobenzene-1-carboperoxoic acid

Product 1

HCID 98453Octahydro-3H-2-benzopyran-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred mixture of 3.16 g (23 mmol) of (3a alpha, 7a alpha )-octahydro-2H-inden-2-one, 17.3 g (207 mmol) of NaHCO3 and 300 mL of dichloromethane was added 9.29 g of 85% m. chloroperoxybenzoic acid in small portions over 15 min. The reaction mixture was stirred for 17 h at 20° C., then 200 mL of 10% aqueous Na2S2O3 was added and, after 15 min, the organic phase was separated. Extraction of the aqueous portion with 2×100 mL of dichloromethane, washing of the combined organic solutions with 10% Na2CO3 and concentration of the dried (MgSO4) solutions under vacuum 9ave 3.51 9 (95%) of racemic (4a alpha, 8a alpha)-octahydro-3H-2-benzopyran-3-one. TLC Rf 0.40 (SiO2, ethyl ether, iodine-brown).

Workup

  1. additionwas added 9.29 g of 85% m
  2. customthe organic phase was separated
  3. extractionExtraction of the aqueous portion with 2×100 mL of dichloromethane
  4. washwashing of the combined organic solutions with 10% Na2CO3 and concentration of the
  5. dry with materialdried (MgSO4) solutions under vacuum 9ave 3.51 9 (95%) of racemic (4a alpha, 8a alpha)-octahydro-3H-2-benzopyran-3-one

Sources & evidence

ORD record
ord-2f9414743b3b443a958f569754e8ca70
Source dataset
uspto-grants-1992_03
Patent number
US05095109

Reaction notes

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