Water → HCID 76585889, compound

HRID 2382523Notes

Reaction equation

HRID 2382523 reaction equation
CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]([CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][C:21]#[C:22][CH2:23][CH:24]([O:50][CH2:51][O:52][CH3:53])[CH:25]1[O:29][CH:28]([CH:30]2[CH2:34][CH2:33][CH:32]([CH:35]([O:46][CH2:47][O:48][CH3:49])[CH2:36][C:37]#[C:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[O:31]2)[CH2:27][CH2:26]1)[CH2:8][C:9]1[C:10](=[O:15])[O:11][CH:12]([CH3:14])[CH:13]=1)(C)C.[H][H].O>C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[OH:6][CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([O:50][CH2:51][O:52][CH3:53])[CH:25]1[O:29][CH:28]([CH:30]2[CH2:34][CH2:33][CH:32]([CH:35]([O:46][CH2:47][O:48][CH3:49])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[O:31]2)[CH2:27][CH2:26]1)[CH2:8][C:9]1[C:10](=[O:15])[O:11][CH:12]([CH3:14])[CH:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 76565468HCID 76565468, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 76585889HCID 76585889, compound

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 241BenzeneSolvent

Procedure

A solution of {2R-[2α[2′R*, 5′R*(R*)], 5β[1(S*),2R*,11R*]}-3-{2-[(1,1-dimethylethyl)diphenylsilyloxy]-11-methoxymethyloxy-11-[octahydro-5′-(1-(methoxymethyloxy)undec-3-ynyl)[2.2′-bifuran]-5-yl]-6-undecen-8-ynyl}-5-methyl-2-(5H)-furanone(64 mg, 70 umole) in benzene (0.5 mL) is stirred at room temperature under a flow of nitrogen while tris(triphenylphosphine)rhodium chloride (14 mg, 15 umole) is added. The mixture is charged with hydrogen gas and stirred at room temperature for two days. Water is added, and the layers are separated. The aqueous extracted with ethyl acetate (3×2 mL) and the combined organic fractions are washed (1×20 mL water) dried (saturated aqueous NaCl, sodium sulfate), filtered, and concentrated. Chromatography (hexane-2:1 hexane:ethyl acetate gradient over silica gel 230-400 mesh) affords the desired product.

Workup

  1. additionis added
  2. customthe layers are separated
  3. extractionThe aqueous extracted with ethyl acetate (3×2 mL)
  4. washthe combined organic fractions are washed (1×20 mL water)
  5. dry with materialdried (saturated aqueous NaCl, sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-968eac4313ef4e0c8b068d648a206c8f
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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