Aluminium lithium hydride → (e)-3-{5-[3,4-Bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}pent-2-en-1-ol

HRID 49368Notes

Reaction equation

HRID 49368 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[O:13][CH2:14][C:15]1[S:19][CH:18]=[C:17](/[C:20](/[CH2:27][CH3:28])=[CH:21]/[C:22](OCC)=[O:23])[CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[CH2:32][O:33][Si:34]([C:37]([CH3:38])([CH3:40])[CH3:39])([CH3:35])[CH3:36])[O:13][CH2:14][C:15]1[S:19][CH:18]=[C:17](/[C:20](/[CH2:27][CH3:28])=[CH:21]/[CH2:22][OH:23])[CH:16]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131724377HCID 131724377, compound

Product 1

HCID 69824522(e)-3-{5-[3,4-Bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}pent-2-en-1-olYield 100%

Procedure

In a manner similar to that of Example 7(b), by reaction of 2.3 g (3.8 mmol) of ethyl (E)-3-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}-2-pentenoate with 180 mg (4.7 mmol) of lithium aluminium hydride, the desired product (m=2.1 g; Y=100%) is obtained in the form of a colourless oil.

Sources & evidence

ORD record
ord-be7615b2cedd4f71a251c7078e0c4b12
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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