(e)-3-{5-[3,4-Bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}pent-2-en-1-ol → HCID 88011850, compound

HRID 49369Notes

Reaction equation

HRID 49369 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][CH:18]=[C:17](/[C:20](/[CH2:24][CH3:25])=[CH:21]/[CH2:22][OH:23])[CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[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][CH:18]=[C:17](/[C:20](/[CH2:24][CH3:25])=[CH:21]/[CH:22]=[O:23])[CH:16]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 69824522(e)-3-{5-[3,4-Bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}pent-2-en-1-ol

Product 1

HCID 88011850HCID 88011850, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

In a manner similar to that of Example 7(c), by reaction of 2.1 g (3.7 mmol) of (E)-3-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}pent-2-en-1-ol with 4.9 g (56 mmol) of manganese dioxide, the crude product (1.8 g) is the expected aldehyde, obtained in a yield of 86%.

Workup

  1. customobtained in a yield of 86%

Sources & evidence

ORD record
ord-069a0a62fd8b411bb0623307cb694731
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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