m-Chloroperbenzoic acid → 3,5-Bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl ester

HRID 1177194Notes

Reaction equation

HRID 1177194 reaction equation
[C:1]([O:5][C:6](=[O:32])[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([CH2:21][CH:22]=[CH2:23])=[C:9]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:41])C=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:32])[C:7]1[CH:8]=[C:9]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:10]([CH2:21][CH:22]2[CH2:23][O:41]2)=[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:12]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 595602714-Allyl-3,5-bis-benzyloxy-benzoic acid tert-butyl ester

Product 1

HCID 595602363,5-Bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl esterYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-allyl-3,5-bis-benzyloxy-benzoic acid tert-butyl ester (200d) (125 g, 0.29 mol) in CH2Cl2 was added m-CPBA (100 g, 0.58 mol) in several portions. The mixture was refluxed overnight. The solid was filtered and washed with CH2Cl2. The combined filtrates were washed with saturated aqueous Na2S2O4 (250 mL) and brine (250 mL). The organic layer was dried over Na2SO4 and concentrated to give a yellow oil. The crude oil was purified by flash column chromatography (EtOAc/petroleum ether=1/20) to give the title compound (75 g, 57.8%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.40 (m, 12H), 5.09 (s, 4H), 3.53 (dd, 1H), 3.17 (m, 1H), 2.80 (dd, H), 2.63 (t, 1H), 2.51 (dd, 1H), 1.60 (s, 9H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe solid was filtered
  3. washwashed with CH2Cl2
  4. washThe combined filtrates were washed with saturated aqueous Na2S2O4 (250 mL) and brine (250 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. customThe crude oil was purified by flash column chromatography (EtOAc/petroleum ether=1/20)

Sources & evidence

ORD record
ord-01bb577cd5cb4d739d3b6325ed7d4d13
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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