HCID 86623587, compound → HCID 68852899, compound

HRID 1986514Notes

Reaction equation

HRID 1986514 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][CH2:6][C:5]([CH:8]([CH3:11])[CH:9]=[O:10])=[C:4]2[C:12]([CH3:18])([CH3:17])[CH:13]3[CH2:16][C:3]12[CH2:15][CH2:14]3.[CH3:20][Mg]Br>C(OCC)C>[CH3:19][C:2]1([CH3:1])[CH2:7][CH2:6][C:5]([CH:8]([CH3:11])[CH:9]([OH:10])[CH3:20])=[C:4]2[C:12]([CH3:18])([CH3:17])[CH:13]3[CH2:16][C:3]12[CH2:15][CH2:14]3

Participants

4

Reactant 2

HCID 86623587HCID 86623587, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68852899HCID 68852899, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

9b (1.7 g, 6.5×10−3 mol) in diethyl ether (50 ml) was added dropwise at 10° C. to a solution of methylmagnesium bromide (3 ml of 3M diethyl ether solution, 9.0×10−3 mol) in the same solvent (50 ml). The reaction mixture was stirred at r. t. for additional 2 h, poured into ice-cold 0.1M HCl (100 ml) and extracted with MTBE (100 ml). The organic phase was washed with brine (2×50 ml), dried (MgSO4), concentrated in vacuo and purified by recrystallisation from hexane to afford 3-(2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undec-5-en-5y-1)butan-2-ol (10b, 1.1 g, 61% yield, white prisms, m.p. 119-121° C.).

Workup

  1. extractionextracted with MTBE (100 ml)
  2. washThe organic phase was washed with brine (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by recrystallisation from hexane

Sources & evidence

ORD record
ord-0c152ebd13684cc58c0919d645330a71
Source dataset
uspto-grants-2009_06
Patent number
US07550417B2

Reaction notes

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