MAGNESIUM SILICATE (synthetic) → 4-Carbomethoxy-3-(3-nitrophenyl)-7-(2-phenylethyl)-7-[(4-phenylphenoxy)methoxy]decan-5-one

HRID 1386840

Reaction equation

HRID 1386840 reaction equation
[C:1]([CH:5]([CH:18]([OH:47])[CH2:19][C:20]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([O:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)[CH2:21][CH2:22][CH3:23])[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH2:7][CH3:8])([O:3][CH3:4])=[O:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[O-][Si]([O-])=O.[Mg+2]>C(Cl)Cl>[C:1]([CH:5]([C:18](=[O:47])[CH2:19][C:20]([CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)([O:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:29][CH:28]=1)[CH2:21][CH2:22][CH3:23])[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH2:7][CH3:8])([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 517045Sodium AcetateHCID 211831244-Carbomethoxy-3-(3-nitrophenyl)-7-(2-phenylethyl)-7-[(4-phenylphenoxy)methoxy]decan-5-olHCID 178418287HCID 178418287, compound

Product 1

HCID 211831254-Carbomethoxy-3-(3-nitrophenyl)-7-(2-phenylethyl)-7-[(4-phenylphenoxy)methoxy]decan-5-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3S),(7R) 4-carbomethoxy-3-(3-nitrophenyl)-7-(2-phenylethyl)-7-[(4-phenylphenoxy)methoxy]decan-5-ol (XIV, EXAMPLE 10, 11.12 g, 79.0 wt %, 13.73 mmol) in methylene chloride (530 ml) is added to a ground mixture of pyridinium chlorochromate (16.099 g, 74.685 mmol, 5.44 eq), sodium acetate (6.984 g, 85.14 mmol, 6.20 eq) and florisil (5.181 g) while maintaining less than 11°. The mixture is warmed to 21° and stirred at 20-25° for 20 hrs. The resultant slurry is filtered through magnesol (47.7 g) and rinsed with methylene chloride (375 ml). The filtrate is concentrated to an oil. An analytical sample of the title compound is obtained by chromatography (ethyl acetate/hexanes): TLC Rf=0.34 (ethyl acetate/hexanes, 10/90); HPLC rt=13.02, 13.23 min; NMR (CDCl3) 8.05-8.01, 7.60-7.00, 5.37, 5.21, 4.03, 3.94, 3.75, 3.58-3.43, 3.39, 2.96, 2.78-1.37, 1.20, 0.91, 0.71-0.61 δ; CMR (CDCl3) 200.89, 200.60, 168.29, 167.81, 157.10, 157.05, 148.38, 148.30, 143.58, 143.32, 141.99, 141.93, 140.73, 140.69, 135.29, 135.01, 134.78, 129.38, 129.23, 128.75, 128.45, 128.36, 128.23, 126.77, 125.91, 125.80, 122.96, 122.80, 122.04, 122.00, 116.16, 87.14, 86.92, 80.93, 80.44, 66.34, 65.92, 52.79, 52.35, 49.02, 48.62, 46.28, 46.20, 38.70, 38.51, 38.43, 37.99, 30.10, 29.52, 26.92, 26.71, 16.64, 16.39, 14.39, 14.16, 11.81, 11.58; MS (CI, ammonia) m/z (relative intensity) 656 (2.8), 655 (6.1), 136 (100).

Workup

  1. temperaturewhile maintaining less than 11°
  2. temperatureThe mixture is warmed to 21°
  3. filtrationThe resultant slurry is filtered through magnesol (47.7 g)
  4. washrinsed with methylene chloride (375 ml)
  5. concentrationThe filtrate is concentrated to an oil

Sources & evidence

ORD record
ord-31b75d2ece6443528daad58aca640917
Source dataset
uspto-grants-2001_07
Patent number
US06265604B1

Linked notes

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