Ethyl Acetate → HCID 86583977, compound

HRID 1270060Notes

Reaction equation

HRID 1270060 reaction equation
C([O:3][C:4](=O)/[CH:5]=[C:6](\[CH3:17])/[C:7]#[C:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)C.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[CH3:17]/[C:6](/[C:7]#[C:8][C:9]1[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([Cl:15])[CH:14]=1)=[CH:5]\[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 86583978HCID 86583978, compound

Product 1

HCID 86583977HCID 86583977, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-3-methyl-5-(3,5-dichloro-phenyl)-pent-2-en-4-ynoic acid ethyl ester (130 mg, 0.46 mmol) in THF (0.5 mL) was added dropwise diisobutylaluminium hydride (1.0 M solution in toluene, 2.1 mL, 2.1 mmol) at −20° C. The reaction mixture was stirred for 2 hours at −20° C., whereafter saturated ammonium chloride was added. The mixture was treated with ethyl acetate and decalite and filtered. The filtrate was evaporated to give crude (E)-3-methyl-5-(3,5-dichloro-phenyl)-pent-2-en-4-yn-1-ol in 113 mg yield.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-af72e463d5d4484d9591cc092d220fd6
Source dataset
uspto-grants-2007_04
Patent number
US07202213B2

Reaction notes

Loading…