Water → HCID 12945490, compound

HRID 1702986Notes

Reaction equation

HRID 1702986 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]2[C:8](=[O:16])[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][CH:4]2[CH2:3]1.[C:17]1([Li])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CCOCC>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]2[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([OH:16])[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][CH:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 12945489HCID 12945489, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 12945490HCID 12945490, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

40 g of 1,2,3,4,4a,10a-hexahydro-2-methyl-5H-[1]-benzothiopyrano[2,3-c]pyridin-5-one were dissolved in 2 liters of dry ether and the solution obtaining was cooled to 5° C. in an ice bath while 220 ml (2 moles) of phenyl lithium were added dropwise thereto over 30 minutes with the temperature held below 0° C. When the addition was complete, the ice bath was removed and the solution thus obtained was stirred at room temperature for 30 minutes. 3 liters of water were added dropwise thereto and the resultant suspension was stirred vigorously for 2 hours and then was filtered. The product was washed with water and ether and was dried to obtain 20.5 g of 2-methyl-5-phenyl-1,3,4,4a,5,10a-hexahydro-2H[1]benzothiopyrano[2,3-c]pyridin-5-ol (37% yield) melting at 176°-181° C.

Workup

  1. customthe solution obtaining
  2. additionwere added dropwise
  3. additionWhen the addition
  4. customthe ice bath was removed
  5. customthe solution thus obtained
  6. filtrationwas filtered
  7. washThe product was washed with water and ether
  8. customwas dried

Sources & evidence

ORD record
ord-97d9bd2835b74c118cf0b5ad75b4b5e8
Source dataset
uspto-grants-1982_09
Patent number
US04350697

Reaction notes

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