(Dimethyl sulfide)trihydroboron → HCID 19888690, compound

HRID 654237Notes

Reaction equation

HRID 654237 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([CH2:12][NH:13][C:14](=O)[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[OH:16])[CH2:8][CH2:7]2.B.CSC>O1CCCC1.CO>[ClH:23].[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([CH2:12][NH:13][CH2:14][CH:15]([OH:16])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 15718614HCID 15718614, compound

Product 1

HCID 19888690HCID 19888690, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the product of step (i) above (1.6 g, 0.0046 mol) in anhydrous tetrahydrofuran (30 ml) is heated to the reflux temperature under nitrogen atmosphere and a mixture of a 10M solution of borane-methyl sulfide (1.4 ml, 0.0014 mol) and anhydrous tetrahydrofuran (10 ml) is slowly dripped in. The obtained solution is refluxed for 4 hours and then diluted with methanol (10 ml). The solvent is evaporated off under vacuum and the obtained residue is dissolved in ethyl ether. The organic solution is made acidic by the addition of HCl saturated isopropanol and the product of the title is obtained therefrom by filtration (0.9 g) M.p. 175°-178° C.

Workup

  1. temperatureThe obtained solution is refluxed for 4 hours
  2. customThe solvent is evaporated off under vacuum
  3. dissolutionthe obtained residue is dissolved in ethyl ether
  4. additionThe organic solution is made acidic by the addition of HCl saturated isopropanol
  5. customthe product of the title is obtained
  6. filtrationby filtration (0.9 g) M.p. 175°-178° C.

Sources & evidence

ORD record
ord-ccfb826efc2040e0a6bdbe802bbe8f7f
Source dataset
uspto-grants-1992_07
Patent number
US05130339

Reaction notes

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