Boron trifluoride etherate → HCID 17979906, compound

HRID 456589Notes

Reaction equation

HRID 456589 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:13]=[CH:12][C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1.B(F)(F)F.CCOCC>C(OCC)C>[O:8]1[C:7]2[CH:12]=[CH:13][C:4]([CH2:2][CH:3]=[O:1])=[CH:5][C:6]=2[O:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 167813336-(Oxiran-2-yl)-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 17979906HCID 17979906, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of crude 6-oxiranyl-2,3-dihydro-benzo[1,4]dioxine (200 mg, 1.12 mmol) in diethyl ether (20 ml) was cooled at −10° C. A 10% solution of boron trifluoride diethyl etherate in diethyl ether (0.16 ml) was then added and the mixture was stirred for 10 minutes at −10° C. The reaction was quenched at this temperature by addition of a saturated aqueous solution of sodium bicarbonate (10 ml). The mixture was extracted twice with diethyl ether. The combined organic phases were washed with water, brine, then dried over magnesium sulfate and evaporated to give crude (2,3-dihydro-benzo[1,4]dioxin-6-yl)-acetaldehyde (191 mg, 95%).

Workup

  1. customThe reaction was quenched at this temperature by addition of a saturated aqueous solution of sodium bicarbonate (10 ml)
  2. extractionThe mixture was extracted twice with diethyl ether
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-b1920ac10ae9429f9475920b6891e4a2
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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