Ethyl Acetate → HCID 86607539, compound

HRID 1179473Notes

Reaction equation

HRID 1179473 reaction equation
Cl[O-].[Na+].[OH:4][CH2:5][C:6]1[C:7](OCOC)=[C:8]([CH:16]2[CH2:20][CH2:19][CH2:18][CH:17]2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][O:31][CH3:32])=[CH:25][CH:24]=2)=[O:22])[CH:9]=[C:10]([O:12][CH2:13][O:14][CH3:15])[CH:11]=1.C[CH2:38][O:39]C(C)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:38][O:39][CH:13]([O:14][CH3:15])[O:12][C:10]1[CH:9]=[C:8]([CH:16]2[CH2:20][CH2:19][CH2:18][CH:17]2[C:21](=[O:22])[C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][O:31][CH3:32])=[CH:27][CH:28]=2)[CH:7]=[C:6]([CH:11]=1)[CH:5]=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23665760Sodium HypochloriteHCID 68527926HCID 68527926, compound

Product 1

HCID 86607539HCID 86607539, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Add sodium hypochlorite (150 mL) to a solution of (±)-[2-(3-hydroxymethyl-2,5-bis-methoxymethoxy-phenyl)-cyclopentyl]-(4-methoxymethoxy-phenyl)-methanone (1.69 g, 3.66 mmol) and tetrabutylammonium bromide (0.500 g, 1.55 mmol) in EtOAc. Stir the biphasic mixture vigorously for 2 hours at ambient temperature and separate the layers. Extract the aqueous solution with EtOAc (50 mL) and wash the combined organics with H2O (50 mL) and brine (25 mL), then dry (MgSO4), filter and concentrate to obtain the subtitled product (1.88 g, >95%) as an oil that may be used without purification. 1H NMR (CDCl3) δ 1.76-1.81 (m, 1H), 1.97-2.14 (m, 4H), 2.24-2.39 (m, 1H), 3.41 (s, 3H), 3.42 (s, 3H), 3.58 (s, 3H), 3.80-3.86 (m, 1H), 4.28-4.33 (m, 1H), 4.94-5.07 (m, 4H), 5,12 (s, 2H), 6.81 (d, J=8.9 Hz, 2H), 7.00 (d, J=3.1 Hz, 1H), 7.08 (d, J=3.1 Hz, 1H), 7.61 (d, J=8.9 Hz, 2H), 10.00 (s, 1H).

Workup

  1. customseparate the layers
  2. extractionExtract the aqueous solution with EtOAc (50 mL)
  3. washwash the combined organics with H2O (50 mL) and brine (25 mL)
  4. dry with materialdry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-eed651f582d944519d8722e90f7d748e
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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