Boron trifluoride etherate → HCID 21804431, compound

HRID 1728973Notes

Reaction equation

HRID 1728973 reaction equation
[SiH](CC)(CC)CC.[CH3:8][CH:9]([CH:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[C:10]([O:12][CH3:13])=[O:11].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 21804430HCID 21804430, compound

Product 1

HCID 21804431HCID 21804431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

132 ml (826 mmol) of HSiEt3 were added to 86 g (413 mmol) of β-hydroxy ester f1 in 800 ml of CH2Cl2. 102 ml (826 mmol) of BF3 -ether were added in portions at -5°--10° C. in the course of 5-10 minutes. After 20 hours at room temperature, the mixture was worked up. After hydrolysis with 220 ml of NaHCO3 (pH 3), the mixture was extracted with ether, and the organic phase was separated off, washed with NaCl solution, dried and distilled (120° C./1 mmHg).

Workup

  1. extractionthe mixture was extracted with ether
  2. customthe organic phase was separated off
  3. washwashed with NaCl solution
  4. customdried
  5. distillationdistilled (120° C./1 mmHg)

Sources & evidence

ORD record
ord-78b5ad1210c4448a957b2e52d8644e96
Source dataset
uspto-grants-1994_07
Patent number
US05329033

Reaction notes

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