4-Nitrobenzoic Acid → HCID 178445823, compound

HRID 1641516Notes

Reaction equation

HRID 1641516 reaction equation
[CH:1]([CH:4]([C@@H:14]1[CH2:17][C@H:16]([OH:18])[CH2:15]1)[C:5]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[O:6][SiH3:7])([CH3:3])[CH3:2].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:18][C@H:16]2[CH2:15][C@H:14]([CH:4]([CH:1]([CH3:2])[CH3:3])[C:5]([CH:11]([CH3:12])[CH3:13])([CH:8]([CH3:9])[CH3:10])[O:6][SiH3:7])[CH2:17]2)=[O:27])=[CH:29][CH:30]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate2×HCID 178445821HCID 178445821, compound

Product 1

HCID 178445823HCID 178445823, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 100 mL flask with cis-3-(triisopropyl-siloxyethyl)cyclobutanol (0.64 g, 2.3 mmol), 4-nitrobenzoic acid (0.79 g, 4.6 mmol) and Ph3P (1.29 g, 4.83 mmol) inside, dry THF 10 mL was added under argon to give a colorless solution. This was cooled to 0° C. and DIAD (1.0 mL, 4.83 mmol) was added drop by drop. After 15 hr, the volatile materials were evaporated and the crude mixture was purified by silica gel flash chromatography (Hexane: EtOAc=20:1 to Hexane: EtOAc=12:1) to give yellow oil contaminated with some DIAD (0.96 g, 97.4%, Rf=0.48 (Hexane: EtOAc=12:1)). 1H NMR (CDCl3, 400 MHz): δ 1.02-1.07 (m, 21H), 1.74-1.79 (m, 2H), 2.24-2.33 (m, 2H), 2.35-2.42 (m, 2H), 2.48-2.60 (m, 1H), 3.67-3.71 (t, J=6.4, 2H), 5.30-5.38 (m, 1H), 8.19-8.28 (m, 4H). 13C NMR (CDCl3, 100 MHz): δ 12.13, 18.19, 25.97, 34.87, 39.08, 61.95, 70.81, 123.66, 130.85, 136.01, 150.65, 164.39. MS (FAB): expected for C22H35NO5Si (M+H)+ 422.60. Found 422.23608. IR (neat) νmax 2942, 2865, 1725, 1608, 1530, 1463, 1349, 1276, 1103, 882, 720, 681.

Workup

  1. customto give a colorless solution
  2. customthe volatile materials were evaporated
  3. customthe crude mixture was purified by silica gel flash chromatography (Hexane: EtOAc=20:1 to Hexane: EtOAc=12:1)
  4. customto give yellow oil

Sources & evidence

ORD record
ord-517b37d808494a4e8ebc5e44fbc97302
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

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