2-[(3-Bromophenyl)methoxy]oxane → 2-(3-Hydroxy-3-(3-((2-tetrahydropyranyloxy)methyl)phenyl)propyl)benzoic acid

HRID 326908

Reaction equation

HRID 326908 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][CH2:21][C:22]1[CH:23]=[C:24]([Mg]Br)[CH:25]=[CH:26][CH:27]=1.BrC1C=C(COC2CCCCO2)C=CC=1>C1COCC1>[OH:1][CH:2]([C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:21][O:20][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)[CH:27]=1)[CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 152820642-[(3-Bromophenyl)methoxy]oxaneHCID 539384212-(3-Oxopropyl)benzoic acidHCID 178419628HCID 178419628, compound

Product 1

HCID 544112982-(3-Hydroxy-3-(3-((2-tetrahydropyranyloxy)methyl)phenyl)propyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

At -10° C., a solution of the aldehyde of Step 4 (5.045 g, 28.3 mmol) in 50 mL of THF was added dropwise to 0.57M 3-((2-tetrahydropyranyloxy)methyl)phenylmagnesium bromide in THF (120 mL, 68.4 mmol, prepared from the bromide of Step 2 and Mg in THF and filtered to remove the excess of Mg) and the mixture as stirred at r.t. for 30 min. At 0° C., 25% aq NH4OAc was added. The title product was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica using acetone: toluene: HOAc 5:95:1 and 15:85:1.

Workup

  1. filtrationfiltered
  2. customto remove the excess of Mg) and the mixture
  3. additionAt 0° C., 25% aq NH4OAc was added
  4. extractionThe title product was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-d8e33f1acad945bbb40926ab0ba800ae
Source dataset
uspto-grants-1993_12
Patent number
US05270324

Linked notes

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