Boron trifluoride etherate → HCID 15056951, compound

HRID 359558Notes

Reaction equation

HRID 359558 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH3:15])[CH:9]=2)[CH:3]1[C:16]([O:18][CH3:19])=[O:17].[CH2:21]([SH:25])[CH2:22][CH2:23][SH:24].B(F)(F)F.CCOCC>C(O)(=O)C.CCOCC>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:3]([C:16]([O:18][CH3:19])=[O:17])[C:2]([CH3:20])([CH3:1])[CH2:7][C:6]3([S:25][CH2:21][CH2:22][CH2:23][S:24]3)[CH:5]=2)=[CH:9][C:10]=1[CH3:15]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 80131,3-PropanedithiolHCID 15125260HCID 15125260, compound

Product 1

HCID 15056951HCID 15056951, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4a (7.75 g, 26.7 mmol) and 1,3-propanedithiol (3.03g, 28.1 mmol) in 50 mL acetic acid was added boron trifluoride etherate (7.98g, 56.2 mmol). The solution was stirred overnight, diluted with ether, washed with H2O saturated NaHCO3, and brine and dried (MgSO4). Removal of the volatile in vacuo provided a residue which was crystallized from hexane, wt 8.0 g, mp 100°-01° C. Anal. C20H25OF2S2 : Theory C: 63.12; H:6.62; S:16.85. Found C: 63.45; H:6.58; S: 16.44.

Workup

  1. washwashed with H2O saturated NaHCO3, and brine
  2. dry with materialdried (MgSO4)
  3. customRemoval of the volatile in vacuo
  4. customprovided a residue which
  5. customwas crystallized from hexane, wt 8.0 g, mp 100°-01° C

Sources & evidence

ORD record
ord-679d669a6e954a15b25c0fdb8348ade2
Source dataset
uspto-grants-1991_03
Patent number
US05001144

Reaction notes

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