Tetrahydrofuran → HCID 59444766, compound

HRID 1363852Notes

Reaction equation

HRID 1363852 reaction equation
[CH3:1]C(C)([O-])C.[K+].C1COCC1.[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Si:33]([O:40][CH:41]1[CH2:52][C:51](=[O:53])[O:50][C@H:49](/[C:54](/[CH3:58])=[CH:55]/[CH:56]=O)[C@@H:48]([CH3:59])[CH:47]=[CH:46][C@@H:45]2[O:60][CH:61]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[O:62][C@:44]2([CH3:69])[CH2:43][CH2:42]1)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]>C(OCC)(=O)C>[Si:33]([O:40][C@H:41]1[CH2:52][C:51](=[O:53])[O:50][C@H:49](/[C:54](/[CH3:58])=[CH:55]/[CH:56]=[CH2:1])[C@@H:48]([CH3:59])[CH:47]=[CH:46][C@@H:45]2[O:60][CH:61]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[O:62][C@:44]2([CH3:69])[CH2:43][CH2:42]1)([C:36]([CH3:38])([CH3:37])[CH3:39])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 59444801HCID 59444801, compound

Product 1

HCID 59444766HCID 59444766, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (38.2 mg, 0.341 mmol) was added to an anhydrous THF (3 ml) solution of methyltriphenylphosphonium iodide (100 mg, 0.247 mmol) at room temperature, and it was stirred at room temperature for 30 minutes. Subsequently, a THF (3 ml) solution of (3aS,4E,6S,7S,13aR)-11-{[tert-butyl(dimethyl)silyl]oxy}-7-[(E)-2-formyl-1-methyletha-1-en-1-yl]-6,13a-dimethyl-2-phenyl-3a,6,7,10,11,12,13,13a-octahydro-9H-[1,3]dioxolo[4,5-f]oxacyclododecin-9-one (150 mg, 0.284 mmol) was added dropwise to this reaction solution at room temperature and the reaction solution was stirred for one hour. The reaction solution was diluted with ethyl acetate and washed with distilled water and brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto, commercial name Silica Gel 60N, 40-100 μm; heptane:ethyl acetate=20:1) to obtain the title compound (44 mg) as a white solid. The title compound was determined to be a mixture of α benzylidene acetal and β benzylidene acetal in a ratio of 1:3.2 by 1H-NMR.

Workup

  1. stirringthe reaction solution was stirred for one hour
  2. washwashed with distilled water and brine
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. filtrationthe drying agent was filtered off
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (Kanto, commercial name Silica Gel 60N, 40-100 μm; heptane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-0701fd7a67f647319236a51bf6c9dc42
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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