Boron trifluoride etherate → HCID 15056951, compound

HRID 2165133Notes

Reaction equation

HRID 2165133 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 (3.03 g, 28.1 mmol) in 50 mL acetic acid was added boron trifluoride etherate (7.98 g, 56.2 mmol). The solution was stirred overnight, diluted with ether, washed with H2O, saturated NaHC3, 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°-101° C. Anal. C20H25FO2S2 : 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 NaHC3, 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°-101° C

Sources & evidence

ORD record
ord-19dde580e042404182d11c493498cd8d
Source dataset
uspto-grants-1990_07
Patent number
US04939143

Reaction notes

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