4-Nitrophenol → 4-Nitrophenyl 5-(1-hydroxysilinan-1-yl)pentanoate

HRID 530152Notes

Reaction equation

HRID 530152 reaction equation
[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.C1(N=C=NC2CCCCC2)CCCCC1.[N+:30]([C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1)([O-:32])=[O:31]>C(OCC)(=O)C>[OH:1][Si:2]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][C:36]2[CH:37]=[CH:38][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=2)=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 904175005-(1-Hydroxysilinan-1-yl)pentanoic acid

Product 1

HCID 904181924-Nitrophenyl 5-(1-hydroxysilinan-1-yl)pentanoateYield 52.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 5-(1-hydroxysilinan-1-yl)pentanoic acid (130 mg, 0.601 mmol) in ethyl acetate (5 mL), N,N′-dicyclohexylcarbodiimide (186 mg, 0.901 mmol) was added. The reaction was stirred under nitrogen at ambient temperature for 30 minutes. After this time, 4-nitrophenol (100 mg, 0.719 mmol) was added, and the reaction was stirred for 16 hours at ambient temperature. After this time, the reaction was filtered to remove any solids, the filter cake was washed with ethyl acetate, and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography eluting with hexanes to 1:3 ethyl acetate/hexanes to afford 4-nitrophenyl 5-(1-hydroxysilinan-1-yl)pentanoate (106 mg, 52%) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 8.26 (dt, J=9.0, 2.5 Hz, 2H), 7.27 (dt, J=9.0, 2.5 Hz, 2H), 2.61 (t, J=7.5 Hz, 2H), 1.84-1.78 (m, 2H), 1.76-1.67 (m, 4H), 1.56-1.44 (m, 4H), 1.40-1.33 (m, 1H), 0.75-0.63 (m, 6H).

Workup

  1. stirringthe reaction was stirred for 16 hours at ambient temperature
  2. filtrationAfter this time, the reaction was filtered
  3. customto remove any solids
  4. washthe filter cake was washed with ethyl acetate
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography
  8. washeluting with hexanes to 1:3 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b82b652907004f7ab9716277ee08c3f5
Source dataset
uspto-grants-2016_05
Patent number
US09352049B2

Reaction notes

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