Boron trifluoride etherate → HCID 68724110, compound

HRID 1471396Notes

Reaction equation

HRID 1471396 reaction equation
O[C@@H:2]1[CH2:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[C@@H:5]([C:12]([O:14][CH3:15])=[O:13])[C:4]([CH3:16])=[CH:3]1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[OH-].[Na+]>ClCCl>[CH3:16][C:4]1[CH:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]2([CH2:11][CH2:2][CH:3]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 131732747HCID 131732747, compound

Product 1

HCID 68724110HCID 68724110, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At −30° C., a solution of crude trans-methyl 9-hydroxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate (1.1 g, 4.9 mmol, prepared as described in the Example 23) in dichloromethane (10 ml) was treated with triethylsilane (4.0 ml, 24.5 mmol) and with BF3.OEt2 (0.92 ml, 7.4 mmol). The resulting mixture was stirred for 45 min. while allowing the temperature to reach 0° C., poured into cold 2N aqueous NaOH (50 ml), and extracted twice with MTBE (25 ml). The combined organic phases were washed with water (25 ml), with a saturated aqueous solution of NaCl (25 ml), dried (MgSO4), and concentrated. FC (55 g SiO2, hexane/MTBE 40:1) of the crude product (1 g) gave methyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (0.92 g, 90%). Boiling point: 98° C. (0.07 mbar).

Workup

  1. customto reach 0° C.
  2. extractionextracted twice with MTBE (25 ml)
  3. washThe combined organic phases were washed with water (25 ml), with a saturated aqueous solution of NaCl (25 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b8bb65566384d6788eb75f78b194020
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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