Tetrahydrofuran → HCID 15695649, compound

HRID 1872434Notes

Reaction equation

HRID 1872434 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](C=O)[C:3]=1C=O.CC(C[AlH]C[CH:18]([CH3:20])[CH3:19])C.C([O:24][CH2:25][CH3:26])(=O)C.[CH2:27]1[CH2:31]O[CH2:29][CH2:28]1>>[CH2:31]([C:25]([OH:24])([CH2:26][CH2:20][CH2:18][CH3:19])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 223252303-Fluorobenzene-1,2-dicarbaldehyde

Product 1

HCID 15695649HCID 15695649, compound

Procedure

To a solution of 22.6 g (69.8 mmol) of the dialdehyde obtained from Step 1 in 650 mL of THF at -60 C. was added 69.8 mL (69.8 mmol) of DIBAL (1M in THF) via a syringe. The reaction mixture was stirred at -40 C. for 20 hours. To the cooled solution at -40 C. was added sufficient amount of ethyl acetate to quench the excess of DIBAL, followed by 3 N HCl. The mixture was extracted with ethyl acetate, washed with water, dried (MgSO4), and concentrated in vacuo. Silica gel chromatographic purification of the crude product gave 13.5 g (58%) of recovered starting material, and 8.1 g (36%) of the desired fluorobenzyl alcohol as a colorless oil: 1H NMR (CDCl3) d 0.88 (t, J=7.05 Hz, 6H), 1.0-1.4 (m, 8H), 1.5-1.72 (m, 4H), 1.94 (br s, 1H), 3.03 (s, 2H), 4.79 (s, 2H), 6.96 (dt, J=8.46, 3.02 Hz, 1H), 7.20 (dd, J=9.47, 2.82 Hz, 1H), 7.42 (dd, J=8.67, 5.64, 1H), 9.40 (s, 1H).

Workup

  1. customto quench the excess of DIBAL
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customSilica gel chromatographic purification of the crude product
  7. customgave 13.5 g (58%)
  8. customof recovered

Sources & evidence

ORD record
ord-59144b3b57df46eb81114578aaac0ea5
Source dataset
uspto-grants-2000_08
Patent number
US06107494

Reaction notes

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