m-Chloroperbenzoic acid → HCID 86622551, compound

HRID 1867224Notes

Reaction equation

HRID 1867224 reaction equation
[CH3:1][CH:2]1[C:6]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[C:5](=[CH2:13])[C:4](=[O:14])[CH2:3]1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl>[CH3:1][C@H:2]1[CH2:3][C:4](=[O:14])[C@@:5]2([O:23][CH2:13]2)[C:6]21[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 216308064-Methyl-1-methylidenespiro[4.6]undecan-2-one

Product 1

HCID 86622551HCID 86622551, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the same general procedure of Example 3, 4-methyl-1-methylenespiro[4.6]undecan-2-one (5.29 g, 27.5 mmol) was reacted with 70% 3-chloroperbenzoic acid (13.6 g, 55.0 mmol) in CH2Cl2 (75 mL+150 mL) at room temp. for 4 d, with additional portions of 70% 3-chloroperbenzoic acid (7.00 g, 28.4 mmol) being added after every day. Work-up with aq. 20% NaHSO3 (250 mL) and purification by silica-gel FC (pentane/Et2O, 9:1, Rf=0.19) provided (3R*,11S*)-11-methyl-1-oxadispiro[2.0.6.3]tridecan-13-one (1.01 g, 18%), besides the (3R*,11R*)-diastereomer (Rf=0.14, 820 mg, 14%).

Workup

  1. additionbeing added after every day
  2. customWork-up with aq. 20% NaHSO3 (250 mL) and purification by silica-gel FC (pentane/Et2O, 9:1, Rf=0.19)

Sources & evidence

ORD record
ord-b5bd2ecd172e486a8ed9cb2b19661220
Source dataset
uspto-grants-2009_12
Patent number
US07632791B2

Reaction notes

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