Sodium Carbonate → 2-(2-Benzyloxy-4-methoxyphenyl)-3-propyloxybenzyl alcohol

HRID 1857564Notes

Reaction equation

HRID 1857564 reaction equation
I[C:2]1[C:9]([O:10][CH2:11][CH2:12][CH3:13])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1B(O)O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].B(O)O>C1(C)C=CC=CC=1.C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[C:2]1[C:9]([O:10][CH2:11][CH2:12][CH3:13])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 118320852-(Benzyloxy)-4-methoxyphenylboronic acidHCID 537480672-Iodo-3-propyloxybenzyl alcohol

Product 1

HCID 536783602-(2-Benzyloxy-4-methoxyphenyl)-3-propyloxybenzyl alcohol

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-iodo-3-propyloxybenzyl alcohol (1.02 g, 3.48 mmol), 2-benzyloxy-4-methoxyphenyl boronic acid (999 mg, 3.83 mmol), Pd(PPh3)4 (200 mg, 0.173 mmol) and 2 M sodium carbonate solution (3.5 ml, 7.96 mmol) was refluxed in toluene (20 ml/ethanol (5 ml) under argon. After 5 hours a further 70 mg of boronic acid was added and refluxing was continued for a further 1 hour. The mixture was cooled, diluted with diethyl ether (200 ml) and washed successively with brine, 5% aqueous sodium hydroxide solution , water and brine and then dried (MgSO4) and concentrated. Purification by chromatography on silica gel gave the title compound as a colourless gum. Yield 1.072 g (81%).

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture was cooled
  3. washwashed successively with brine, 5% aqueous sodium hydroxide solution , water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-5c6260b649eb42ce862a3abd14d3cf76
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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