Ethyl acetate hexane → HCID 59271890, compound

HRID 1893186Notes

Reaction equation

HRID 1893186 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[H][H].CCOC(C)=O.CCCCCC>C(O)C.[Pt]>[CH3:18][C:2]([CH3:1])([CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 59271792HCID 59271792, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59271890HCID 59271890, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl (2E)-4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enoate (23 g, 90 mmol) and 5% Pt on carbon (3 g, 14.65 mmol) in ethanol (200 mL) was shaken on the Parr under 45 psi of hydrogen for 5 days (complete conversion by TLC: 10% EtOAc/hexane-no UV active spots). The catalyst was filtered off catalyst and the filtrate concentrated. Drying under vacuum gave ethyl 4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentanoate as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 4.7 (t, 1H), 4.12 (q, 2H), 3.8 (m, 1H), 3.5 (m, 1H), 3.4 (d, 1H), 3.0, (d, 1H), 2.3 (m, 2H), 1.8 (m, 1H), 1.7-1.5 (m, 6H), 1.9 (s, 3H), 1.88 (s, 3H).

Workup

  1. filtrationThe catalyst was filtered off catalyst
  2. concentrationthe filtrate concentrated
  3. customDrying under vacuum

Sources & evidence

ORD record
ord-05922fdce75345498c7178b29a22051b
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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