HCID 54518441, compound → HCID 19785650, compound

HRID 256616Notes

Reaction equation

HRID 256616 reaction equation
[S:1]1[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[CH:15][CH2:16][CH:17]([OH:27])[C:18]2[CH:19]=[C:20]([Si:23]([CH3:26])([CH3:25])[CH3:24])[O:21][CH:22]=2)[CH:13]=[O:14])=[CH:4][C:3]2[CH:28]=[CH:29][CH:30]=[CH:31][C:2]1=2>C1C=CC=CC=1>[S:1]1[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:13]([OH:14])[O:27][CH:17]([C:18]3[CH:19]=[C:20]([Si:23]([CH3:26])([CH3:25])[CH3:24])[O:21][CH:22]=3)[CH2:16][CH:15]=2)=[CH:4][C:3]2[CH:28]=[CH:29][CH:30]=[CH:31][C:2]1=2

Participants

3

Reactant 1

HCID 54518441HCID 54518441, compound

Product 1

HCID 19785650HCID 19785650, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(6-(Benzo(b]thien-2-yl)-hexyl]-5-hydroxy-5-(2-trimethylsilyl-4-furyl)-2-pentenal (0.142 g., 0.31 mmol) was dissolved in 30 ml anhydrous benzene, placed in a quartz tube, and subjected to four freeze, pump, thaw cycles. The tube was flushed with argon and irradiated at 254 nm for 2.5 hours. The solution was concentrated to give an orange gum. This material was purified by flash chromatography (silica, 5 to 30% ethyl acetate/hexane. First eluted was the desired hydroxy acetal as a yellow gum. Second eluted was starting aldehyde as a clear gum.

Workup

  1. customplaced in a quartz tube
  2. customThe tube was flushed with argon
  3. customirradiated at 254 nm for 2.5 hours
  4. concentrationThe solution was concentrated
  5. customto give an orange gum
  6. customThis material was purified by flash chromatography (silica, 5 to 30% ethyl acetate/hexane
  7. washFirst eluted
  8. washSecond eluted

Sources & evidence

ORD record
ord-0afcf3a21f954cc99b08ab3cab115b7a
Source dataset
uspto-grants-1993_11
Patent number
US05258400

Reaction notes

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