(e)-3-{5-[3,4-Bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}pent-2-en-1-ol → HCID 88011784, compound

HRID 49333Notes

Reaction equation

HRID 49333 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=1[CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[O:13][CH2:14][C:15]1[S:19][C:18](/[C:20](/[CH2:24][CH3:25])=[CH:21]/[CH2:22][OH:23])=[CH:17][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=1[CH2:29][O:30][Si:31]([C:34]([CH3:35])([CH3:37])[CH3:36])([CH3:32])[CH3:33])[O:13][CH2:14][C:15]1[S:19][C:18](/[C:20](/[CH2:24][CH3:25])=[CH:21]/[CH:22]=[O:23])=[CH:17][CH:16]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 69825143(e)-3-{5-[3,4-Bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}pent-2-en-1-ol

Product 1

HCID 88011784HCID 88011784, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2.74 g (5.1 mmol) of (E)-3-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}pent-2-en-1-ol are dissolved in 80 mL of dichloromethane and placed under a nitrogen atmosphere. 4.45 g (51 mmol) of manganese dioxide are added and the medium is stirred for 14 hours. After filtration and then evaporation, a yellow oil is obtained. The crude product (2.9 g) is the expected aldehyde, obtained in a quantitative yield.

Workup

  1. filtrationAfter filtration
  2. customevaporation
  3. customa yellow oil is obtained
  4. customobtained in a quantitative yield

Sources & evidence

ORD record
ord-f532658f0633418d9484d7cfb4c99f62
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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