Triphenylphosphine → HCID 178445771, compound

HRID 713916Notes

Reaction equation

HRID 713916 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5]2.[C:14]([C@@H:18]1[CH2:23][CH2:22][C@H:21](O)[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O.C1(C)C=CC=CC=1>[C:14]([C@H:18]1[CH2:23][CH2:22][C@H:21]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5]3)[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 45894766-Hydroxy-2-naphthonitrileHCID 5363146Diisopropyl azodicarboxylateHCID 178445811HCID 178445811, compound

Product 1

HCID 178445771HCID 178445771, compoundYield 146.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a vial charged with 6-hydroxy-2-naphthonitrile (3.38 g, 0.02 mol, 1.0 eq.), cis-4-tert-butylcyclohexanol (6.24 g, 0.04 mol, 2.0 eq.), PPh3 (10.5 g, 0.04 mol, 2.0 eq.) and toluene (20 mL), was added DIAD (12 mL, 0.06 mol, 3.0 eq.) under nitrogen atmosphere at r.t. and stirred for 15 h. Water was added and extracted with EtOAc. The organic layer was purified by silica gel chromatography (PE:EA=10:1) to give the title compound (9.0 g, 86%) as a slight yellow solid. EDI-MS (M+1)+: 308.0. 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 7.78-7.73 (m, 2H), 7.54 (dd, 1H), 7.22 (dd, 1H), 7.14 (s, 1H), 4.33-4.30 (m, 1H), 2.29-2.25 (m, 2H), 1.93-1.90 (m, 2H), 1.48-1.26 (m, 2H), 1.25-1.10 (m, 3H), 0.91 (s, 9H).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was purified by silica gel chromatography (PE:EA=10:1)

Sources & evidence

ORD record
ord-6c9da274b10342d8be0d0f9ff8492cdd
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

Loading…