Cornforth reagent → HCID 86762465, compound

HRID 1028862Notes

Reaction equation

HRID 1028862 reaction equation
C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O.[C:22]1([NH:32][C:33](=[O:44])[O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][OH:43])=[CH:38][CH:37]=2)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1>ClCCl.C(OCC)C>[C:22]1([NH:32][C:33](=[O:44])[O:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([CH:42]=[O:43])=[CH:40][CH:41]=2)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 86762464HCID 86762464, compound

Product 1

HCID 86762465HCID 86762465, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

PDC (2.1 g, 5.6 mmol) was added to a stirred mixture of alcohol 7 (1.72 g, 5.6 mmol) and activated 4 Å molecular sieves (1.0 g) in anhydrous dichloromethane (20 mL). The resulting mixture was stirred for 5 h; then it was diluted with diethyl ether (20 mL). The resulting suspension was filtrated through a pad of silica gel. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (hexanes/ethyl acetate=5:1) to provide aldehyde 6 (1.46 g, 4.8 mmol) as a white solid in 85% yield: m.p.: 153-154° C.; IR (thin film): 3272, 1691, 1609, 1544, 1504, 1257, 1206 cm−1; 1H NMR (500 MHz, CDCl3): δ 10.01 (s, 1H), 7.93-7.81 (m, 5H), 7.68 (d, J=8.2 Hz, 1H), 7.57 (s, 1H), 7.55-7.40 (m, 4H), 5.32 (s, 2H) ppm; 13C NMR (101 MHz, CDCl3): δ 192.07, 192.03, 154.26, 143.05, 136.09, 134.16, 132.34, 130.94, 130.08, 128.82, 128.28, 126.74, 126.41, 126.20, 125.83, 125.47, 120.68, 119.36, 66.35 ppm. HRMS (m/z): [M+Na]+ calcd. for C19H15NNaO3, 328.0944; found, 328.0938.

Workup

  1. filtrationThe resulting suspension was filtrated through a pad of silica gel
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica gel (hexanes/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-9f6f15ec8f69448c9ffdbdc892b16fb2
Source dataset
uspto-grants-2014_05
Patent number
US08735622B2

Reaction notes

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