Diethyl Ether → HCID 11206192, compound

HRID 842433Notes

Reaction equation

HRID 842433 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][C@H:13]1[CH2:18][C@@H:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C@H:16]([CH3:24])[CH2:15][CH2:14]1.C(OCC)C.[O-][Si]([O-])=O.[Mg+2]>C(Cl)Cl>[CH3:24][C@@H:16]1[CH2:15][CH2:14][C:13](=[O:12])[CH2:18][C@H:17]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 61680MAGNESIUM SILICATE (synthetic)HCID 12017029HCID 12017029, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 11206192HCID 11206192, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of pyridinium chlorochromate (36.0 g, 167 mmol) in methylene chloride (200 mL) was added 10 (17.27 g, 92.8 mmol), whereupon the mixture became a dark homogenous solution. The reaction was stirred overnight. Diethyl ether (3×300 mL) was added and the product was passed through a short column of florisil to remove the chromium salts. Removal of the solvent in vacuo gave an oil (15.9 g, 93% yield). This was carried onto the next step without further purification. Rf 0.61 (ethyl acetate/hexane 3:7); 1H NMR (300 MHz, CDCl3) δ 4.18 (dq, J=1.1, 7.2, 2H), 2.35-2.63 (m, 5H), 2.01-2.19 (m, 2H), 1.42-1.53 (m, 1H), 1.28 (t, J=7.2, 3H), 1.03 (d, J=6.4, 3H); 13C NMR (75 MHz, CDCl3) δ 208.9, 173.5, 60.6, 50.5, 42.7, 40.3, 33.4, 33.2, 19.0, 14.1; MS (EI) m/z 184 (M+, 23), 169 ([M-CH3]+, 3), 155 ([M-CH2CH3]+, 8), 139 ([M-OCH2CH3]+, 8), 128 (35), 111 (100), 99 (46). 55 (50); [α]D−46.9° (c=1.00, CH2Cl2). Analysis calc'd for C10H16O3: C, 65.19; H, 8.75. Found: C, 65.06; H, 8.73.

Workup

  1. customto remove the chromium salts
  2. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-2de5f49e4c0f4cbab6689c0ab6a01a1a
Source dataset
uspto-grants-2002_04
Patent number
US06375943B1

Reaction notes

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