Boron trifluoride → HCID 70977307, compound

HRID 2402386Notes

Reaction equation

HRID 2402386 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[O:11]=[C:12]1[CH2:21][CH2:20][CH2:19][C:18]2[CH:17]=[C:16]([C:22]([O:24][CH3:25])=[O:23])[CH:15]=[CH:14][C:13]1=2.B(F)(F)F.C(=O)=O.CC(C)=O>C1COCC1.CO>[OH:11][C:12]1([C:7]2[S:6][CH:10]=[CH:9][N:8]=2)[CH2:21][CH2:20][CH2:19][C:18]2[CH:17]=[C:16]([C:22]([O:24][CH3:25])=[O:23])[CH:15]=[CH:14][C:13]1=2

Participants

8

Reactant 5

HCID 6356Boron trifluorideHCID 9256ThiazoleHCID 15309116Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylateHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 70977307HCID 70977307, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium (2.3 M in hexanes) is pumped (push-pull syringe-pump) to a ⅛″ tee with a pressure gauge and 2 feet of ⅛″ stainless steel tubing (for pre-cooling). This tubing is connected to a ¼ inch T-mixer. Thiazole (0.5 M in THF) is pumped using a pump, 100 μL head (Fluid Metering, Inc., Syosset, N.Y. USA) to 2 feet of ⅛″ stainless steel tubing (for pre-cooling) connected to the same T-mixer. The T-mixer is connected to a static mixer ¼-34 (5.3 mL) (Koflo Corporation, Cary, Ill. USA) connected to a ¼″ elbow and ¼″ stainless steel tubing of 6 inches in length (3.3 mL). This 6-inch length tubing is connected to another ¼″ T-mixer which is also connected to a feed of methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate and BF3 (0.5 M in THF, pumped with a FMI pump, 100 μL head), and to a second static mixer Koflo ¼-34 (5.3 mL) followed by a “loop” of ¼″ stainless steel (2.5 ft length, 16.8 mL). The reactor has a total volume of 30.7 mL, and is placed into a cold bath at −45° C. (±5° C., dry ice/acetone). The outlet stream is then connected to a ⅛″ T-mixer (outside of the cold bath) fed with methanol (FMI pump, 100 μL head) for in situ quenching, and is finally collected into an extractor containing MTBE and aqueous phosphoric acid (1.5 M). A flow diagram of the assembly is shown in FIG. 1.

Workup

  1. customis placed into a cold bath at −45° C.
  2. customquenching
  3. customis finally collected into an extractor
  4. additioncontaining MTBE and aqueous phosphoric acid (1.5 M)

Sources & evidence

ORD record
ord-002558ddfc2c473d9d7a1c7966e354d4
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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