Triphenylphosphine → HCID 15758918, compound

HRID 1627928Notes

Reaction equation

HRID 1627928 reaction equation
[Cl:1][C:2]1[C:3]([CH2:9][CH2:10][CH2:11][OH:12])=[C:4](O)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:9][CH2:10][CH2:11][O:12]2

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 59606751HCID 59606751, compound

Product 1

HCID 15758918HCID 15758918, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-2-(3-hydroxypropyl)phenol (0.56 g; 3 mmol) and triphenylphosphine (1.02 g; 3.90 mmol) in tetrahydrofuran (42 mL) was added diisopropyl azadicarboxylate (0.766 mL; 3.90 mmol), the reaction mixture was stirred at room temperature for 4 h and the volatiles were removed under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-80%) in heptane furnished 0.121 g (24%) of 5-chlorochroman.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-80%) in heptane

Sources & evidence

ORD record
ord-2c3a23a64b074301968dca593d86a714
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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