Water → HCID 53685925, compound

HRID 1614733Notes

Reaction equation

HRID 1614733 reaction equation
[O:1]([CH2:8][C:9]#[C:10]/[CH:11]=[CH:12]\[C:13]#[C:14][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O[Li].O>C1COCC1.CCOCC>[O:1]([CH2:8][C:9]#[C:10][CH:11]=[CH:12][C:13]#[CH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86746682HCID 86746682, compound

Product 1

HCID 53685925HCID 53685925, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step (b) (5.0 g, 19.7 mmol) in 20 mL THF was added 5 mL of water and LiOH-H2O (5.6 g, 133 mmol). The solution was stirred for 4 h, diluted with ether and washed with water. The aqueous layer extracted with ether and then ethyl acetate. The organic fractions were combined, dried (MgSO4) and concentrated. The residue was chromatographed over silica (30:1 hexane/ethyl acetate) to give 3.37 g of (94%) of 7-phenoxy-3-heptene-1,5-diyne.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer extracted with ether
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica (30:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fbc990ff9b3143f5b9411c28ac0abdb1
Source dataset
uspto-grants-1993_03
Patent number
US05198560

Reaction notes

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