Sodium hydride → HCID 23523001, compound

HRID 392845Notes

Reaction equation

HRID 392845 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[I-].[Li+].[C:11]1([C@H:17]2[C@H:22]([O:23][CH3:24])[C@H:21]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[CH2:20][CH2:19][C:18]2=[O:35])[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1>CS(C)=O.C1COCC1>[C:11]1([C@H:17]2[C@H:22]([O:23][CH3:24])[C@H:21]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[CH2:20][CH2:19][C@:18]32[O:35][CH2:2]3)[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 66321Lithium iodideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23522995HCID 23522995, compound

Product 1

HCID 23523001HCID 23523001, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

385 mg (1.74 mmol) of trimethylsulphoxonium iodide are added to a suspension of sodium hydride (28 mg, 1.16 mmol) in 1 mL of DMSO. The mixture is stirred for 40 minutes, followed by successive addition of 1 mL of THF and 186 mg of anhydrous lithium iodide. The mixture is stirred for a further 30 minutes, cooled to 0° C., and 39 mg (0.11 mmol) of (2S,3S,4R)-2-(cyclohex-1-enyl)-3-methoxy-4-p-methoxybenzyloxy-cyclohexanone dissolved in 0.5 mL of THF are added. The bath is removed and the reaction is allowed to continue for 40 minutes at room temperature. After adding pH 7 buffer, extracton and evaporation of the solvents, the product is purified by chromatography on a preparative silica plate (eluent: 1:1 ether/pentane) to give 19 mg (45%) of (3R,4S,5S,6R)-4-(cyclohex-1-enyl)-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2,5]octane in the form of a colourless oil.

Workup

  1. stirringThe mixture is stirred for a further 30 minutes
  2. additionare added
  3. customThe bath is removed
  4. waitto continue for 40 minutes at room temperature
  5. additionAfter adding pH 7 buffer
  6. customextracton and evaporation of the solvents
  7. customthe product is purified by chromatography on a preparative silica plate (eluent: 1:1 ether/pentane)

Sources & evidence

ORD record
ord-eae7570ce8e646ff89ca501ccd14643f
Source dataset
uspto-grants-2004_10
Patent number
US06803382B2

Reaction notes

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