HCID 10921539, compound → 40317-08-6

HRID 413929Notes

Reaction equation

HRID 413929 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 1N 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. 1H NMR (CDCl3, 300 MHz) δ: 2.20 (bs, 1H), 4.25 (d, 2H), 5.95 (dt, 1H, Jtrans=15 Hz), 6.35 (dt, 1H, Jtrans=15 Hz), 7.23-7.35 (m, 3H), 7.35-7.48 (m, 2H).

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-fdd4e5147faa464f926250d5adcae461
Source dataset
uspto-grants-2003_05
Patent number
US06569901B2

Reaction notes

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