HCID 59545204, compound → HCID 45258940, compound

HRID 1960103Notes

Reaction equation

HRID 1960103 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@@H:7]([CH2:14]/[CH:15]=[C:16](/[CH3:20])\[CH2:17][CH:18]=[CH2:19])[C:8](N(OC)C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:23][Mg]Cl>C1COCC1>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@@H:7]([CH2:14]/[CH:15]=[C:16](/[CH3:20])\[CH2:17][CH:18]=[CH2:19])[C:8](=[O:9])[CH3:23])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 59545204HCID 59545204, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 45258940HCID 45258940, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a THF (300 mL) solution of the starting material 5 (152.6 g, 465 mmol) was slowly added methylmagnesium chloride (200 mL, 3.0 M in THF, 600 mmol) in 30 min at 0° C. The reaction was stirred over 30 min at 0° C., and was carefully quenched with saturated ammonium chloride water solution (300 mL). Its pH was then adjusted to 7 with 1N hydrochloric acid. Volatiles were removed via a rotavap. The residue was extracted with diethyl ether (1 L). Ethereal extracts were washed with water and brine, dried over magnesium sulfate. Flash chromatography on silica gel (0-3% ethyl acetate in hexanes) afforded the desired product 6 as pale yellow oil (125 g, 95%).

Workup

  1. customin 30 min
  2. customat 0° C
  3. customwas carefully quenched with saturated ammonium chloride water solution (300 mL)
  4. customVolatiles were removed via a rotavap
  5. extractionThe residue was extracted with diethyl ether (1 L)
  6. washEthereal extracts were washed with water and brine
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-2fe87963a43b467b971a0ed39a687d9f
Source dataset
uspto-grants-2013_04
Patent number
US08410305B2

Reaction notes

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