Diethyl Ether → HCID 15398356, compound

HRID 2111468Notes

Reaction equation

HRID 2111468 reaction equation
[C-:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[C-:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)[CH:2]=[CH:3][CH:4]=[CH:5]1.[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 131725737HCID 131725737, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15398356HCID 15398356, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A sample of 4-ferrocenylbenzyl alcohol 16 (630 mg, 2.15 mmol) was added to a suspension of pyridinium chlorochromate (1.22 g, 3.23 mmol) in CH2Cl2 (5 mL) and the mixture was stirred under argon at rt for 18 h. Then Et2O (20 mL) was added and the mixture was filtered through a pad of Celite. The filtrate was concentrated and chromatographed (silica, CH2Cl2/hexanes, 4:1) affording 306 mg (47.8%). TLC (silica, CH2Cl2), Rf=0.35; mp 122-125° C. (lit.35a 121-125° C.); 1H NMR δ 4.07 (s, 5H), 4.46 (A2B2, J=1.5 Hz, 2H), 4.47 (A2B2, J=1.5 Hz, 2H), 7.60, 7.78 (AA′BB′, J=8.7 Hz, 4H), 9.97 (s, 1H); 13C NMR δ 67.8, 70.5, 70.6, 70.8, 127.0, 127.7, 130.7, 130.7, 134.7, 192.5; EI-MS obsd 290.0406 (M+), calcd exact mass 290.0394; Anal. Calcd for C17H14FeO: C, 70.37; H, 4.86. Found: C, 70.50; H, 4.81.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. customchromatographed (silica, CH2Cl2/hexanes, 4:1)
  4. customaffording 306 mg (47.8%)
  5. custommp 122-125° C. (lit.35a 121-125° C.)

Sources & evidence

ORD record
ord-ab358c4d09bb49d1a11e04c02d6db465
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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