Benzyl 5-(1-hydroxysilinan-1-yl)pentanoate → 5-(1-Hydroxysilinan-1-yl)pentanoic acid

HRID 530151Notes

Reaction equation

HRID 530151 reaction equation
[OH:1][Si:2]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]CC2C=CC=CC=2)=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>C(O)C.[Pd]>[OH:1][Si:2]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 90417551Benzyl 5-(1-hydroxysilinan-1-yl)pentanoate

Product 1

HCID 904175005-(1-Hydroxysilinan-1-yl)pentanoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To benzyl 5-(1-hydroxysilinan-1-yl)pentanoate (205 mg, 0.669 mmol) in ethanol (6 mL), palladium on activated carbon (10%, wet, 41 mg) was added. The reaction was stirred under hydrogen (1 atm) at room temperature for 16 hours. After this time, the reaction was filtered through Celite® and the filter cake washed with methanol. The filtrate was concentrated under reduced pressure to afford 5-(1-hydroxysilinan-1-yl)pentanoic acid (140 mg, 97%) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ Exchangeable protons not observed (2H), 2.38-2.32 (m, 2H), 1.78-1.61 (m, 6H), 1.48-1.31 (m, 4H), 0.80-0.54 (m, 6H); ESI MS m/z=215 [M−H]−.

Workup

  1. filtrationAfter this time, the reaction was filtered through Celite®
  2. washthe filter cake washed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fdfbff7b648c46bd8f7a93c08e640d1e
Source dataset
uspto-grants-2016_05
Patent number
US09352049B2

Reaction notes

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