5-Hydroxy-2-(4-methyl-3-pentenyl)-5-(2-trimethylsilyl-4-furyl)-2-pentenal → 3,6-Dihydro-6-hydroxy-5-(4-methyl-3-pentenyl)-2-(2-trimethylsilyl-4-furyl)-2H-pyran

HRID 256619Notes

Reaction equation

HRID 256619 reaction equation
[OH:1][CH:2]([C:14]1[CH:15]=[C:16]([Si:19]([CH3:22])([CH3:21])[CH3:20])[O:17][CH:18]=1)[CH2:3][CH:4]=[C:5]([CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH:6]=[O:7]>C1C=CC=CC=1>[OH:7][CH:6]1[O:1][CH:2]([C:14]2[CH:15]=[C:16]([Si:19]([CH3:22])([CH3:21])[CH3:20])[O:17][CH:18]=2)[CH2:3][CH:4]=[C:5]1[CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12]

Participants

3

Reactant 1

HCID 572176475-Hydroxy-2-(4-methyl-3-pentenyl)-5-(2-trimethylsilyl-4-furyl)-2-pentenal

Product 1

HCID 197856343,6-Dihydro-6-hydroxy-5-(4-methyl-3-pentenyl)-2-(2-trimethylsilyl-4-furyl)-2H-pyran

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-Hydroxy-2-(4-methyl-3-pentenyl)-5-(2-trimethylsilyl-4-furyl)-2-pentenal (0.88 g, 0.274 mmol) was dissolved in 27 ml anhydrous benzene, placed in a quartz tube and deoxygenated by saturating with oxygen-free nitrogen for one hour. The solution was irradiated at 254 nm for three hours, cooled and concentrated to give a brown-yellow gum. This material was purified by flash chromatography (silica, 15 to 30% ethyl acetate/hexane). First eluted was the desired acetal followed by starting aldehyde.

Workup

  1. customplaced in a quartz tube
  2. customdeoxygenated
  3. concentrationby saturating with oxygen-free nitrogen for one hour
  4. customThe solution was irradiated at 254 nm for three hours
  5. temperaturecooled
  6. concentrationconcentrated
  7. customto give a brown-yellow gum
  8. customThis material was purified by flash chromatography (silica, 15 to 30% ethyl acetate/hexane)
  9. washFirst eluted

Sources & evidence

ORD record
ord-cf417b4cd8f24b0b9ed083a180f0b512
Source dataset
uspto-grants-1993_11
Patent number
US05258400

Reaction notes

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