Acetaldehyde → HCID 67692756, compound

HRID 1033084Notes

Reaction equation

HRID 1033084 reaction equation
[CH:1](=O)[CH3:2].[CH2:4]([O:7][CH2:8][CH:9]1[S:14](=[O:16])(=[O:15])[C:13]2[S:17][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:19][C:12]=2[CH:11]([NH2:24])[CH2:10]1)[CH:5]=[CH2:6].[BH4-].[Na+].Cl>O1CCCC1.C(O)C>[CH2:4]([O:7][CH2:8][CH:9]1[S:14](=[O:16])(=[O:15])[C:13]2[S:17][C:18]([S:20]([NH2:23])(=[O:21])=[O:22])=[CH:19][C:12]=2[CH:11]([NH:24][CH2:1][CH3:2])[CH2:10]1)[CH:5]=[CH2:6]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67826396HCID 67826396, compound

Product 1

HCID 67692756HCID 67692756, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetaldehyde, 1.5 ml. (1.19 g, 0.027 m), was added to a solution of 5,6-dihydro-6-allyloxymethyl-4-amino-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide, 10.0 g. (0.028 m.), in dry tetrahydrofuran, 150 ml., and the mixture was stirred at ambient temperature for 0.75 h. under nitrogen. The solution was added over 15 min. to a stirred suspension of sodium borohydride, 5.3 g. (0.14 m.) in absolute ethanol, 150 ml., at 0° C. After stirring for an additional 15 min. at 0° C., the mixture was treated dropwise with 10% hydrochloric acid, 35 ml., until gas evolution ceased. After concentration in vacuo, the residue was distributed between 200 ml. of water containing 10 ml. of 3N hydrochloric acid and 75 ml. of ethyl acetate. The ethyl acetate layer was washed with 100 ml. of water, the combined aqueous wash and acidic water layer were basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (300 ml. and 2×200 ml.). After washing twice with brine and drying over sodium sulfate, ethyl acetate was evaporated in vacuo to yield 6.6 g. (63%) of the mixture of isomers as a yellow foam.

Workup

  1. customat 0° C
  2. stirringAfter stirring for an additional 15 min. at 0° C.
  3. concentrationAfter concentration in vacuo
  4. washThe ethyl acetate layer was washed with 100 ml
  5. washof water, the combined aqueous wash
  6. extractionextracted with ethyl acetate (300 ml. and 2×200 ml.)
  7. washAfter washing twice with brine
  8. dry with materialdrying over sodium sulfate, ethyl acetate
  9. customwas evaporated in vacuo
  10. customto yield 6.6 g

Sources & evidence

ORD record
ord-ae393372b6b240dc81381cff73d6a7b2
Source dataset
uspto-grants-1994_05
Patent number
US05308863

Reaction notes

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