HCID 10921539, compound → 40317-08-6

HRID 1270051Notes

Reaction equation

HRID 1270051 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14](=O)/[CH:15]=[CH:16]/[C:17]#[C:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C>C1COCC1>[C:19]1([C:18]#[C:17]/[CH:16]=[CH:15]/[CH2:14][OH:13])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 10921539HCID 10921539, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 546319840317-08-6Yield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminium hydride (1.0 M solution in toluene, 42 mL, 42 mmol) was added, under a nitrogen atmosphere at −70° C., to a stirred solution of (E)-5-phenyl-pent-2-en-4-ynoic acid ethyl ester (1.2 g, 5.99 mmol) in dry THF (105 mL). After stirring for 1.5 h, the reaction mixture was quenched with methanol (5 mL) followed by saturated aqueous Rochelle's salt (90 mL) and 1 N sodium hydroxide (40 mL). The organic phase was separated, and the aqueous phase extracted with ethyl acetate (250 mL, 2×). The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give 948 mg (100%) of (E)-5-phenyl-pent-2-en-4-yn-1-ol.

Workup

  1. customthe reaction mixture was quenched with methanol (5 mL)
  2. customThe organic phase was separated
  3. extractionthe aqueous phase extracted with ethyl acetate (250 mL, 2×)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-248d021e69db42d390ea821d17c6a04b
Source dataset
uspto-grants-2007_04
Patent number
US07202213B2

Reaction notes

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