Hydrochloric Acid → HCID 20398644, compound

HRID 462502Notes

Reaction equation

HRID 462502 reaction equation
C([Li])CCC.CCCCCC.C[Si](C)(C)[N:14]1[CH2:19][CH2:18][C:17]2[S:20][CH:21]=[CH:22][C:16]=2[CH2:15]1.[B:25](OCCCC)([O:31]CCCC)[O:26]CCCC.Cl>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[S:20]1[C:17]2[CH2:18][CH2:19][NH:14][CH2:15][C:16]=2[CH:22]=[C:21]1[B:25]([OH:31])[OH:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 12712Tributyl borateHCID 13055412HCID 13055412, compoundHCID 178418339Butyllithium

Product 1

HCID 20398644HCID 20398644, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-20 °C

Procedure

45.4 cc. of a 12% solution of butyl lithium in hexane (0.084 mol) are added dropwise, under an atmosphere of nitrogen, to a solution, cooled to -20° C., of 15 g. (0.07 mol) 5-trimethylsilyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, prepared as in Example 7, in 150 cc. of THF. The reaction mixture is allowed to return to 0° C. and 3 cc. HMPT are added thereto. After cooling this mixture to -50° C., a solution of 19.3 g. (0.084 mol) tributyl borate in 30 cc. THF is added dropwise. Stirring is continued for 2 hours, whilst allowing the mixture to return to ambient temperature. 28 cc. 3N hydrochloric acid (0.084 mol) are then added and the precipitate formed is filtered off. The crystals are washed with acetone and with diisopropyl ether and then dried in vacuo. Off white crystals are obtained in quantitative yield; m.p.>260° C.; NMR (D2O): 6.75 (s,1H); 4.10 (m,2H); 2.80-3.50 (m,4H).

Workup

  1. customto return to 0° C.
  2. temperatureAfter cooling this mixture to -50° C.
  3. customto return to ambient temperature
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. washThe crystals are washed with acetone and with diisopropyl ether
  7. customdried in vacuo
  8. customOff white crystals are obtained in quantitative yield

Sources & evidence

ORD record
ord-4d8280bcfdab41a29063dd63ba5456e3
Source dataset
uspto-grants-1985_05
Patent number
US04515951

Reaction notes

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