Boron trifluoride etherate → HCID 131727263, compound

HRID 2382524Notes

Reaction equation

HRID 2382524 reaction equation
[CH3:1][C:2]([CH:5]([CH2:14][CH2:15][C:16]#[CH:17])[CH2:6][CH2:7][C:8]#[C:9][O:10][SiH:11]([CH3:13])[CH3:12])([CH3:4])[CH3:3].C([Li])CCC.B(F)(F)F.C[CH2:28][O:29][CH2:30]C.[CH:32]([CH:34]1[O:38][CH:37]([CH:39]2[CH2:43][CH2:42][CH:41]([CH:44]([O:55]COC)[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[O:40]2)[CH2:36][CH2:35]1)=[O:33].[NH4+].[Cl-]>C1COCC1>[CH3:4][C:2]([CH:5]([CH2:14][CH2:15][C:16]#[C:17][CH:32]([O:33][CH2:28][O:29][CH3:30])[CH:34]1[O:38][CH:37]([CH:39]2[CH2:43][CH2:42][CH:41]([CH:44]([OH:55])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[O:40]2)[CH2:36][CH2:35]1)[CH2:6][CH2:7][C:8]#[C:9][O:10][SiH:11]([CH3:12])[CH3:13])([CH3:1])[CH3:3]

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherateHCID 25517Ammonium ChlorideHCID 76565465HCID 76565465, compoundHCID 131727264HCID 131727264, compoundHCID 178418339Butyllithium

Product 1

HCID 131727263HCID 131727263, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 5-(1,1-dimethylethyl)dimethylsilyloxynona-1,8-diyne (1.80 g, 10 mmol) in THF (10 mL) is stirred at −78° C. while a solution of n-butyllithium (2.0M in hexanes, 4.95 mL) is added. The mixture is stirred for ten minutes at −78 degrees C. and boron trifluoride etherate (9.9 mmol, 1.25 mL) is added. After another thirty minutes stirring at −78° C., a solution of 5-formyl-octahydro-5′-(1-methoxymethoxy undecyl)-[2.2′]-bifuran (1.35 g, 3.5 mmol) in THF (8 mL) is added. The resulting solution is stirred at −78° C. for four hours, and is poured into an aqueous solution of NH4Cl (100 mL, 2.0 M). The mixture is extracted with ethyl acetate (3×100 mL) and the combined organic fractions are washed (1× water), filtered, (saturated aqueous NaCl, sodium sulfate) and concentrated. Chromatography (hexane-2:1 hexane:ethyl acetate gradient over silica gel 230-400 mesh) affords 5-(1,1-dimethylethyl)dimethylsilyloxy-10-methoxymethoxy-10-[octahydro-5′-(1-hydroxyundecyl) [2.2′-bifuran]-5-yl]deca-1,8-diyne as an oil.

Workup

  1. additionis added
  2. stirringAfter another thirty minutes stirring at −78° C.
  3. stirringThe resulting solution is stirred at −78° C. for four hours
  4. extractionThe mixture is extracted with ethyl acetate (3×100 mL)
  5. washthe combined organic fractions are washed (1× water)
  6. filtrationfiltered
  7. concentration(saturated aqueous NaCl, sodium sulfate) and concentrated

Sources & evidence

ORD record
ord-e4bdf98c0ce84dd9983e08aa365ff341
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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