HCID 72615805, compound → HCID 69552354, compound

HRID 984539Notes

Reaction equation

HRID 984539 reaction equation
[C:1]([O:4][CH:5]([CH2:15][CH:16]=[C:17]([CH3:25])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:24])[CH:22]=[O:23])[C:6]([CH3:14])=[CH:7][C:8]1[N:9]=[C:10]([CH3:13])[S:11][CH:12]=1)(=[O:3])[CH3:2].[CH3:26][O:27][C:28](=[O:47])[CH2:29][C@H:30]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[C:31]([CH3:38])([CH3:37])[C:32](=[O:36])[CH:33](Br)[CH3:34]>C1COCC1.[Cl-].[Na+].O>[CH3:26][O:27][C:28](=[O:47])[CH2:29][CH:30]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:41])[CH3:42])[C:31]([CH3:37])([CH3:38])[C:32](=[O:36])[CH:33]([CH3:34])[CH:22]([OH:23])[CH:21]([CH3:24])[CH2:20][CH2:19][CH2:18][C:17]([CH3:25])=[CH:16][CH2:15][CH:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]([CH3:14])=[CH:7][C:8]1[N:9]=[C:10]([CH3:13])[S:11][CH:12]=1

Participants

5

Reactant 2

HCID 72615805HCID 72615805, compoundHCID 86591974HCID 86591974, compound

Product 1

HCID 69552354HCID 69552354, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 240 mg (1.95 mmol) CrCl2 and 125 mg (0.93 mmol) in 10.0 mL absolute THF was added 322 mg (0.886 mmol) 3-acetoxy-2,6,10-trimethyl-1-(2-methyl-thiazol-4-yl)-11-oxo-undeca-1,5-diene (8 b) in 1.0 mL absolute THF and 384 mg (0.971 mmol) (3S)-6-bromo-3-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-5-oxo-heptanoic acid methyl ester (235) at ambient temperature. After stirring for 2 h 15 min at ambient temperature, 12 mL brine were added and stirring was continued for five minutes. The waterphase was extracted five times with 15 mL of a pentane-diethylether-mixture (1:5) and the combined organic layers were washed twice with 20 mL demi water and twice with 20 mL brine. After drying over Na2SO4, filtration and concentrating in vacuo, the obtained oil was purified by flash chromatography (column dimensions: 2.0×20.0 cm, diethylether/petroleum ether=5:4).

Workup

  1. stirringstirring
  2. waitwas continued for five minutes
  3. extractionThe waterphase was extracted five times with 15 mL of a pentane-diethylether-mixture (1:5)
  4. washthe combined organic layers were washed twice with 20 mL demi water and twice with 20 mL brine
  5. dry with materialAfter drying over Na2SO4, filtration
  6. concentrationconcentrating in vacuo
  7. customthe obtained oil was purified by flash chromatography (column dimensions: 2.0×20.0 cm, diethylether/petroleum ether=5:4)

Sources & evidence

ORD record
ord-17a9be30f6c34ac8b70fd7bb9d749f2d
Source dataset
uspto-grants-2005_03
Patent number
US06867333B2

Reaction notes

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