Tetrahydrofuran → HCID 86679295, compound

HRID 1519737Notes

Reaction equation

HRID 1519737 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.C([Si]([C:34]#[C:35][C:36]1[CH:37]=[C:38]([CH:41]=[O:42])[O:39][CH:40]=1)(C(C)C)C(C)C)(C)C.C1COCC1.[Cl-].[NH4+]>O.C(OCC)C.C(O)(=O)C>[C:35]([C:36]1[CH:37]=[C:38]([CH:41]=[O:42])[O:39][CH:40]=1)#[CH:34]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 11078149TBAF tetrahydrofuranHCID 86679294HCID 86679294, compound

Product 1

HCID 86679295HCID 86679295, compoundYield 80.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A 1 mol/L-TBAF-THF solution (3.4 mL) was added dropwise, under ice cooling, to a mixture of 4-[(triisopropylsilanyl)ethynyl]furan-2-carbaldehyde (0.63 g) as obtained in Example 24-(1), THF (3.0 mL) and acetic acid (0.20 mL) over the course of 1.5 hours. Diethyl ether and water were added to the reaction mixture, and the mixture was adjusted to pH 5 with a saturated aqueous solution of ammonium chloride to isolate the organic layer. The extract was washed with brine, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=100/0→80/20) to obtain 4-ethynylfuran-2-carbaldehyde (brown solid) (0.22 g, 80%).

Workup

  1. customto isolate the organic layer
  2. washThe extract was washed with brine
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=100/0→80/20)

Sources & evidence

ORD record
ord-8da6824a460d471bb5f12cff73285735
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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