Benzoic Acid → HCID 86602886, compound

HRID 1819395Notes

Reaction equation

HRID 1819395 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@@H:30]1[CH2:35][CH2:34][CH2:33][C@H:32]([C:36]#[N:37])[CH2:31]1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O>[C:36]([C@H:32]1[CH2:33][CH2:34][CH2:35][C@H:30]([O:8][C:1](=[O:9])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:31]1)#[N:37]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23584546HCID 23584546, compound

Product 1

HCID 86602886HCID 86602886, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzoic acid (1.1 g, 8.8 mmol) and PS-triphenylphosphine (6.7 g, 15.5 mmol) in anhydrous THF (40 mL) was added cis-3-hydroxy-cyclohexanecarbonitrile (1.1 g, 8.8 mmol) in anhydrous THF (20 mL). The reaction mixture was cooled while diethyl azodicarboxylate (DEAD) (1.9 mL, 12.3 mmol) was added by syringe over 3 min. The reaction was shaken for 12 h. The mixture was filtered and the resin was washed with ether. The filtrate was concentrated in vacuo to afford an oily solid. Silica gel column chromatography using 95:5 hexanes:EtOAc as an eluent afforded 0.29 g (14%) of benzoic acid trans-3-cyano-cyclohexyl ester as a white solid.

Workup

  1. additionwas added by syringe over 3 min
  2. filtrationThe mixture was filtered
  3. washthe resin was washed with ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto afford an oily solid

Sources & evidence

ORD record
ord-405138ab0be54a82b8041e50cc40843d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…