HCID 67019287, compound → HCID 67019292, compound

HRID 1753995Notes

Reaction equation

HRID 1753995 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][C:5]1[C:6](=O)[CH2:7][CH2:8][CH2:9][C:10]=1[O:11]CC(C)C.[CH2:18]([Li])[CH3:19]>CCOCC>[CH2:18]([C:6]1[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:5]=1[CH2:4][CH2:3][CH:2]([CH3:1])[CH3:17])[CH3:19]

Participants

4

Reactant 2

HCID 67019287HCID 67019287, compoundHCID 178506846HCID 178506846, compound

Product 1

HCID 67019292HCID 67019292, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of isobutyl ether 8 (88.0 g, 370 mmol) in anhydrous ether (250 mL) was cooled to 0° C. in an ice bath and treated dropwise with ethyl lithium (650 mL). The resulting mixture was stirred at 0° C. for 2 hours and then at room temperature for 48 hours. The reaction mixture was slowly quenched with water (200 mL) and extracted with ether (2×200 mL). The combined organic layer was dried (Na2SO4) and concentrated under vacuum to provide 75 g of crude oil, which was purified by chromatography (silica gel; hexane/ether 4:1) to give 58.0 g (80.1%) of 9 as an oil: MS m/z 195 (M+1); 1H NMR (300 MHz, CDCl3) δ 2.4-2.3 (m, 4H), 2.3-2.2 (m, 4H), 1.95-1.85 (m, 2H), 1.6-1.5 (m, 1H), 1.2-1.1 (m, 2H), 1.1 (t, 3H), 0.9 (d, 6H); 13C NMR (CDCl3) δ 199.2, 159.9, 135.4, 39.0, 38.1, 30.0, 28.5, 27.8, 22.9, 22.6, 22.5, 12.4.

Workup

  1. waitat room temperature for 48 hours
  2. customThe reaction mixture was slowly quenched with water (200 mL)
  3. extractionextracted with ether (2×200 mL)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customto provide 75 g of crude oil, which
  7. customwas purified by chromatography (silica gel; hexane/ether 4:1)

Sources & evidence

ORD record
ord-bf5841b9b49d4c1595711156de37e304
Source dataset
uspto-grants-2015_10
Patent number
US09169190B2

Reaction notes

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