Potassium Hydroxide → HCID 59697113, compound

HRID 661801Notes

Reaction equation

HRID 661801 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]#[C:15][Si](C)(C)C)=[CH:8][CH:7]=1>O.C1COCC1>[C:12]([C:9]1[CH:8]=[CH:7][C:6]([C:5]([OH:20])=[O:4])=[CH:11][CH:10]=1)#[C:13][C:14]#[CH:15]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59697118HCID 59697118, compound

Product 1

HCID 59697113HCID 59697113, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium hydroxide (3.700 g, 65.9 mmol) was dissolved in H2O (10 mL) and added to a solution of 4∝-trimethylsilanyl-buta-1,3-diynyl)-benzoic acid methyl ester 3 (3.420 g, 13.5 mmol) in THF (26 mL) in the absence of light. After stirring 16 h, the reaction was quenched with 1.0 M HCl (120 mL) and the resulting precipitate was filtered, washed with 1:1 hexanes/benzene (150 mL) and dried in vacuo to afford 2.100 g (91% yield, 98% pure) of 4-(buta-1,3-diynyl)-benzoic acid 4 as a brown solid, mp>230° C. Although diyne 4 was found to be unstable at room temperature it could be stored for several weeks at 0° C. with only small amounts of decomposition observed by TLC. Rf=0.2 (4:1 Hexanes/EtOAc); HPLC (300 nm, 28 min run) 16.0 min; LRMS (ES+) m/z 171.0 (C11H6O2+H requires 171.04).

Workup

  1. customthe reaction was quenched with 1.0 M HCl (120 mL)
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with 1:1 hexanes/benzene (150 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-07c1710af7a24c41be18dc61fe9fea1b
Source dataset
uspto-grants-2011_12
Patent number
US08084615B2

Reaction notes

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