HCID 57845584, compound → HCID 57814829, compound

HRID 1254173Notes

Reaction equation

HRID 1254173 reaction equation
[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[C@@H:5]([CH2:19][OH:20])[C@H:4]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:3]1.[H][H]>CCOC(C)=O.O=[Pt]=O>[Cl:1][C@H:2]1[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])[C@@H:5]([CH2:19][OH:20])[C@H:4]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:3]1

Participants

5

Reactant 2

HCID 57845584HCID 57845584, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57814829HCID 57814829, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1 g (2.49 mmol) of alcohol 4 in 13 mL of EtOAc and Adam's catalyst (22 mg) was stirred under 30 psi of hydrogen gas in a Parr apparatus over 21 h. The mixture was then filtered to remove the catalyst through a plug of silica gel with EtOAc as solvent. The filtrate was then concentrated in vacuo yield the propyl ester 11 (990 mg) as an oil; 1H NMR (CDCl3); 0.94 (t, J=7.3 Hz, 3H), 1.20-1.94 (m, 31H), 2.17 (m, 2H), 2.32 (m, 4H), 3.46-4.12 (m, 8H), 4.03 (t, J=6.6 Hz, 2H), 4.13-4.38 (m, 2H), 4.59 (m, 1H), 4.73 (m, 1H).

Workup

  1. filtrationThe mixture was then filtered
  2. customto remove the catalyst through a plug of silica gel with EtOAc as solvent
  3. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-de3e9e53d55d4665bd2d2c127f52d2a6
Source dataset
uspto-grants-2013_06
Patent number
US08455547B2

Reaction notes

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