Ethyl Acetate → 2-[[(4S,5R)-5-[(1E,3E)-1,3-hexadien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid

HRID 1354484Notes

Reaction equation

HRID 1354484 reaction equation
C[Si](C)(C)[C:3]#[C:4]/[CH:5]=[CH:6]/[CH:7]=[CH:8]/[C@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@H:10]1[CH2:16][O:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.[Cl-].[NH4+]>C1COCC1.O.[OH-].[Na+]>[CH:8](/[C@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@H:10]1[CH2:16][O:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:7]\[CH:6]=[CH:5]\[C:4]#[CH:3]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 865887722-[[(4S,5R)-5-[(1E,3E)-6-(trimethylsilyl)-1,3-hexadien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, 1,1-dimethylethyl ester

Product 1

HCID 865887712-[[(4S,5R)-5-[(1E,3E)-1,3-hexadien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-[[(4S,5R)-5-[(1E,3E)-6-(trimethylsilyl)-1,3-hexadien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, 1,1-dimethylethyl ester in THF was treated with a solution of tetrabutylammonium fluoride in THF in portions. The reaction mixture was then stirred overnight. The reaction mixture was diluted with water and 1 N NaOH solution (1:1) and stirred overnight. The reaction mixture was poured into a mixture of ethyl acetate and saturated ammonium chloride. The aqueous layer was washed with ethyl acetate (2×). The combined organic layers were washed with water and brine solution, dried, treated with silica gel and concentrated to give 2.8 g of 2-[[(4S,5R)-5-[(1E,3E)-1,3-hexadien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, a compound of formula (V), as an oil: 1H NMR (CDCl3) δ 1.37 (s, 3H), 1.46 (s, 3H), 3.06 (s, 1H), 3.49 (m, 2H), 4.06 (m, 2H), 4.37 (m, 1H), 4.65 (t, 1H), 5.54 (d, 1H), 5.66 (dd, 1H), 6.28 (dd, 1H), 6.58 (dd, 1H) ppm.

Workup

  1. stirringstirred overnight
  2. washThe aqueous layer was washed with ethyl acetate (2×)
  3. washThe combined organic layers were washed with water and brine solution
  4. customdried
  5. additiontreated with silica gel
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55ede6156f384bfb8ee549a78b39110f
Source dataset
uspto-grants-2007_05
Patent number
US07223798B2

Reaction notes

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