Boron trifluoride etherate → HCID 68725689, compound

HRID 1471385Notes

Reaction equation

HRID 1471385 reaction equation
O[CH:2]1[CH2:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]([CH3:17])=[CH:3]1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[CH3:17][C:4]1[CH:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2([CH2:11][CH2:2][CH:3]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 68722661HCID 68722661, compound

Product 1

HCID 68725689HCID 68725689, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At −20° C., a solution of ethyl 9-hydroxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate (1.5 g, 6.3 mmol, cis/trans 34:66, prepared as described in example 16) in dichloromethane was treated with successively with triethylsilane (3.66 g, 31.5 mmol) and with BF3.OEt2 (1.34 g, 9.4 mmol). The resulting solution was stirred for 45 min., poured into an ice-cold 2M aqueous NaOH solution (50 ml), and extracted twice with MTBE (40 ml). The organic phases were washed with water (40 ml), with a saturated aqueous solution of NaCl (40 ml), dried (MgSO4) and concentrated. FC (100 g SiO2, hexane/MTBE 25:1) of the crude product (1.28 g) gave ethyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (0.98 g, 70%).

Workup

  1. extractionextracted twice with MTBE (40 ml)
  2. washThe organic phases were washed with water (40 ml), with a saturated aqueous solution of NaCl (40 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d4155107f1e6407ba35c3d5aeec890b2
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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