2-(3-Bromophenoxy)tetrahydro-2H-pyran → 2(3-Hydroxy-3-(3-(2-tetrahydropyranyloxy)phenyl)propyl)benzoic acid

HRID 258474Notes

Reaction equation

HRID 258474 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][C:21]1[CH:22]=[C:23]([Mg]Br)[CH:24]=[CH:25][CH:26]=1.BrC1C=C(C=CC=1)OC1CCCCO1>C1COCC1>[OH:1][CH:2]([C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([O:20][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)[CH:26]=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 50672642-(3-Bromophenoxy)tetrahydro-2H-pyranHCID 539384212-(3-Oxopropyl)benzoic acidHCID 178419632HCID 178419632, compound

Product 1

HCID 197372822(3-Hydroxy-3-(3-(2-tetrahydropyranyloxy)phenyl)propyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

At -10° C., a solution of the aldehyde of Step 2 (5.045 g, 28.3 mmol) in 50 mL of THF was added dropwise to 0.57M 3-(2-tetrahydropyranyloxy)phenylmagnesium bromide in THF (120 mL, 68.4 mmol, prepared from 2-(3-bromophenoxy)tetrahydropyran and Mg in THF and filtered to remove the excess of Mg) and the mixture was 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:AcOH 5:95:1 and 15:85:1. Yield: 9.74 g, 97%.

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-63794b18735d431597f10788a32947b5
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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