Tetrahydrofuran → Methyl 5-Acetoxy-2-bromomethyl-4-methoxyhydrocinnamate

HRID 1898764Notes

Reaction equation

HRID 1898764 reaction equation
[OH:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]([CH2:14]O[Si](C(C)(C)C)(C)C)=[C:6]([CH:13]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].C1C[O:28][CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:50]>CCOCC>[C:27]([O:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]([CH2:14][Br:50])=[C:6]([CH:13]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])(=[O:28])[CH3:26]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23372374Methyl 5-Hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

Product 1

HCID 23372383Methyl 5-Acetoxy-2-bromomethyl-4-methoxyhydrocinnamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of methyl 5-hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate (5.21 g) in carbon tetrabromide (12.35 g) in anhydrous ether (75 ml) and anhydrous THF (50 ml) is added portionwise triphenylphosphine (9.78 g) and the mixture stirred at room temperature for 60 minutes, diluted with ether, then filtered. The filtrate is concentrated in vacuo and the residue purified by filtration through silica gel in 50% ethyl acetate in hexanes followed by HPLC, eluting with 25% ethyl acetate in hexanes, to give the desired product.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo
  3. filtrationthe residue purified by filtration through silica gel in 50% ethyl acetate in hexanes
  4. washeluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-94763bb1c83c48a3b83869585f59d137
Source dataset
uspto-grants-1996_11
Patent number
US05571506

Reaction notes

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