Triphenylphosphine → HCID 59578574, compound

HRID 1774567Notes

Reaction equation

HRID 1774567 reaction equation
[Cl:1][C:2]1[C:7](O)=[C:6]([CH2:9][CH2:10][CH2:11][OH:12])[C:5]([CH3:13])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[C:7]2[O:12][CH2:11][CH2:10][CH2:9][C:6]=2[C:5]([CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59578505HCID 59578505, compound

Product 1

HCID 59578574HCID 59578574, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, a solution of 6-chloro-2-(3-hydroxypropyl)-3-methylphenol (7c) (6.74 g, 33.6 mmol) in anhydrous tetrahydrofuran (500 mL) was cooled to 0° C. Triphenylphosphine (11.45 g, 43.7 mmol) was added, followed by diisopropyl azodicarboxylate (8.60 mL, 43.7 mmol). The reaction mixture was stirred for 16 hours at room temperature. After concentration in vacuo, the residue was dissolved in diethyl ether and the precipitate was filtered off. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 90/10), to provide 8-chloro-5-methyl-3,4-dihydro-2H-1-benzopyran (7d) (5.74 g, 31.4 mmol, 94%), as a light yellow oil.

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue was dissolved in diethyl ether
  3. filtrationthe precipitate was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 90/10)

Sources & evidence

ORD record
ord-c9962d16004f4e1796a7bdc6e8766d28
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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