Triphenylphosphine → Ethyl acetate hexane

HRID 511945Notes

Reaction equation

HRID 511945 reaction equation
Br[C:2]1[CH:11]=[CH:10]C=C2[C:3]=1[CH:4]=[CH:5]C=[C:7]2[CH2:12][OH:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:33]([O:37]C(NC(NC(OC(C)(C)C)=O)=N)=O)(C)(C)[CH3:34].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1.O>[CH3:34][CH2:33][O:37][C:12]([CH3:7])=[O:13].[CH3:10][CH2:11][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 18963829(5-Bromonaphthalen-1-yl)methanolHCID 135638421tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamate

Product 1

HCID 21226206Ethyl acetate hexaneYield 243.9%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 1140TolueneSolvent

Procedure

(5-Bromonaphthalen-1-yl)methanol (275 mg), PPh3 (456 mg, 1.5 eq.), and 1,3-bis(t-butoxycarbonyl)guanidine (601 mg, 2 eq.) in 5 mL toluene at 0° C. was added diisopropylazodicarboxylate (0.34 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 20% EtOAc/hexane yielding product as a white solid (493 mg, 90% yield). 1H NMR (400 MHz) (CDCl3) δ 9.47 (bs, 2H), 8.11 (d, J=8 Hz, 1H), 7.91 (d, J=8 Hz, 1H), 7.73 (d, J=8 Hz, 1H), 7.46 (t, J=16 Hz, 1H), 7.28 (t, J=16 Hz, 1H), 7.16 (d, J=8 Hz, 1H), 5.62 (s, 2H), 1.36 (s, 9H), 1.07 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ160.83, 154.95, 135.04, 131.95, 129.89, 126.71, 126.26, 126.16, 123.71, 122.87, 122.73, 84.19, 79.03, 45.10, 28.23, 27.61.

Workup

  1. customReaction
  2. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-57d612b5b7f14ae2836eb240540fd98c
Source dataset
uspto-grants-2015_08
Patent number
US09102617B2

Reaction notes

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