Triphenylphosphine → Ethyl acetate hexane

HRID 511949Notes

Reaction equation

HRID 511949 reaction equation
C[C:2]1[CH:7]=[C:6](C(F)(F)F)[CH:5]=[CH:4][C:3]=1C1C=CC=C2C=1C=CC=[C:17]2[CH2:22][OH:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:43]([O:47]C(NC(NC(OC(C)(C)C)=O)=N)=O)(C)(C)[CH3:44].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1.O>[CH3:44][CH2:43][O:47][C:22]([CH3:17])=[O:23].[CH3:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67998505(5-(2-Methyl-4-(trifluoromethyl)phenyl)naphthalen-1-yl)methanolHCID 135638421tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamate

Product 1

HCID 21226206Ethyl acetate hexaneYield 251.9%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 1140TolueneSolvent

Procedure

(5-(2-Methyl-4-(trifluoromethyl)phenyl)naphthalen-1-yl)methanol (67 mg), PPh3 (83 mg, 1.5 eq.), and 1,3-bis(t-butoxycarbonyl)guanidine (110 mg, 2 eq.) in 3 mL toluene at 0° C. was added diisopropylazodicarboxylate (0.06 mL, 1.5 eq.) drop wise over 15 minutes. Reaction was stirred for 3 hours at room temperature then 2 drops H2O were added, and the solution was concentrated. Chromatography achieved using ISCO max gradient 30% EtOAc/hexane yielding product as a clear oil (93 mg, 79% yield). 1H NMR (400 MHz) (CDCl3) δ 9.55 (bs, 2H), 8.10 (d, J=8 Hz, 1H), 7.62-7.57 (m, 3H), 7.41-7.22 (m, 5H), 5.84-5.74 (m, 2H), 2.06 (s, 3H), 1.48 (s, 9H), 1.17 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ163.80, 160.97, 155.04, 138.98, 137.77, 135.08, 131.60, 130.85, 130.69, 126.61, 126.20, 125.71, 125.37, 124.60, 122.88, 122.45, 122.23, 84.03, 78.99, 45.23, 28.26, 27.57, 19.93.

Workup

  1. customReaction
  2. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-7ff80fb107714d029bef606b4017509c
Source dataset
uspto-grants-2015_08
Patent number
US09102617B2

Reaction notes

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