Triphenylphosphine → HCID 86710806, compound

HRID 1400747Notes

Reaction equation

HRID 1400747 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].[CH3:10][C@@H:11](O)[CH2:12][CH:13]=[CH2:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][C@H:13]([CH2:12][CH:11]=[CH2:10])[CH3:14]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 6999724(2R)-pent-4-en-2-olHCID 132842722-Bromo-5-chlorophenol

Product 1

HCID 86710806HCID 86710806, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-5-chlorophenol (0.40 g, 1.93 mmol, 1 equiv), (R)-pent-4-en-2-ol (0.397 mL, 3.86 mmol, 2 equiv), and PPh3 (1.01 g, 3.86 mmol, 2 equiv) in THF (6.4 mL) was added DEAD (0.61 mL, 3.86 mmol, 2 equiv). After stirring 20 h, reaction diluted with ether and washed with 1 N NaOH. The ether layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-10% EtOAc in hexane) to provide the product as a colorless oil (0.49 g, 92%). 1H NMR (400 MHz, CDCl3) δ 7.45 (d, J=8.3 Hz, 1H), 6.89 (d, J=2.3 Hz, 1H), 6.83 (dd, J=8.5, 2.3 Hz, 1H), 5.90 (ddt, J=17.1, 10.1, 7.2 Hz, 1H), 5.21-5.11 (m, 2H), 4.49-4.39 (m, 1H), 2.60-2.50 (m, 1H), 2.48-2.38 (m, 1H), 1.37 (d, J=6.3 Hz, 3H).

Workup

  1. customreaction
  2. washwashed with 1 N NaOH
  3. dry with materialThe ether layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography (0-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-7b3a3eb402b140fc9474d5a0fc9c3879
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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