Tetrahydrofuran → ethyl 4-(hydroxy(tetrahydro-2H-pyran-4-yl)methyl)benzoate

HRID 1892706Notes

Reaction equation

HRID 1892706 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[O:19])[CH2:14][CH2:13]1.[CH2:20]1COCC1>>[OH:19][CH:18]([CH:15]1[CH2:16][CH2:17][O:12][CH2:13][CH2:14]1)[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH2:9][CH3:20])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 69273Methyl 4-iodobenzoateHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 68156522ethyl 4-(hydroxy(tetrahydro-2H-pyran-4-yl)methyl)benzoate

Procedure

To a solution of methyl 4-iodobenzoate (1.21 mL, 7.24 mmol) in THF (12 ml) at −40° C. was added TurboGrignard (1.3 M in THF, 6.13 ml, 7.97 mmol) dropwise. The mixture was stirred for approximately 60 minutes whereupon, tetrahydro-2H-pyran-4-carbaldehyde (0.761 ml, 0.724 mmol) was added dropwise. The mixture was stirred for 15 minutes and slowly warmed to rt over 12 hours. The reaction was quenched with HCl (1 N, aq.) and the aq. layer was extracted with EtOAc (3×75 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide ethyl 4-(hydroxy(tetrahydro-2H-pyran-4-yl)methyl)benzoate. Crude mixture used into the next step without any further purification.

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched with HCl (1 N, aq.)
  3. extractionthe aq. layer was extracted with EtOAc (3×75 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d67103f416e644d6a9fe3b8d65b8d717
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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