Phenol → HCID 58031844, compound

HRID 535271Notes

Reaction equation

HRID 535271 reaction equation
[OH:1][CH2:2][C:3]1([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:20]#[C:21][CH3:22])[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=2)[CH2:5][CH2:4]1.[C:23]1(O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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>C(Cl)Cl>[O:1]([CH2:2][C:3]1([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([CH:14]([C:20]#[C:21][CH3:22])[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:13]=2)[CH2:5][CH2:4]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58031834HCID 58031834, compound

Product 1

HCID 58031844HCID 58031844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg of methyl 3-[4-(1-hydroxymethylcyclopropylmethoxy)phenyl]hex-4-ynoate were dissolved in 10 ml of DCM and used to charge a microwave vessel, then 46.7 mg of phenol and 130 mg of triphenylphosphine (polymer-bound, Reagentplus 99%) were added, and the mixture was stirred for 10 min to swell the resin. Subsequently, 98 μl of diisopropyl azodicarboxylate were added and the mixture was stirred at 120° C. under microwave irradiation for 15 min. The cooled reaction mixture was filtered and the filtercake was washed 3× with 10 ml each time of DCM. The combined filtrates were washed with 30 ml of water, then dried using a ChemElut cartridge and concentrated under reduced pressure. The residue was purified by means of RP-HPLC. This gave 68 mg of methyl 3-[4-(1-phenoxymethylcyclopropylmethoxy)phenyl]hex-4-ynoate.

Workup

  1. additionto charge a microwave vessel
  2. stirringthe mixture was stirred at 120° C. under microwave irradiation for 15 min
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. washthe filtercake was washed 3× with 10 ml each time of DCM
  6. washThe combined filtrates were washed with 30 ml of water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by means of RP-HPLC

Sources & evidence

ORD record
ord-d0c81baec6f94a36a697a879e51ac902
Source dataset
uspto-grants-2014_10
Patent number
US08859494B2

Reaction notes

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