Sodium Thiosulfate → 2-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetaldehyde
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Si:23]([O:30][CH2:31][CH2:32][C:33]1[S:37][C:36]([CH2:38][CH2:39][OH:40])=[CH:35][CH:34]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[Si:23]([O:30][CH2:31][CH2:32][C:33]1[S:37][C:36]([CH2:38][CH:39]=[O:40])=[CH:35][CH:34]=1)([C:26]([CH3:28])([CH3:27])[CH3:29])([CH3:25])[CH3:24]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Dess-Martin periodinane (0.38 g) was added to a solution of 2-(5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethanol (example 4, step f) (0.22 g) in dichloromethane (5 mL) and the resulting mixture stirred for 30 min. A mixture of saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (25 mL) were added and the resulting mixture stirred for 10 min. The organic layer was separated and washed with a solution of saturated sodium bicarbonate solution (10 mL), and brine (10 mL), then dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a clear oil which was used immediately. Yield 0.21 g.
Workup
- additionwere added
- stirringthe resulting mixture stirred for 10 min
- customThe organic layer was separated
- washwashed with a solution of saturated sodium bicarbonate solution (10 mL), and brine (10 mL)
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-18a41acd02fc4465beb09b97bdfb18e3
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629271B2
Reaction notes
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