Sodium Hydroxide → HCID 88011818, compound

HRID 49366Notes

Reaction equation

HRID 49366 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:36]=[CH:37][C:38]=1[CH2:39][O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[O:13][CH2:14][C:15]1[S:19][C:18](/[C:20](/[CH2:34][CH3:35])=[CH:21]/[C:22]#[C:23][C:24]([C:30]([F:33])([F:32])[F:31])([OH:29])[C:25]([F:28])([F:27])[F:26])=[CH:17][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O-].[Na+].[OH-].[Na+]>C1COCC1.O>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:36]=[CH:37][C:38]=1[CH2:39][O:40][Si:41]([C:44]([CH3:45])([CH3:47])[CH3:46])([CH3:42])[CH3:43])[O:13][CH2:14][C:15]1[S:19][C:18](/[C:20](/[CH2:34][CH3:35])=[CH:21]/[CH:22]=[CH:23]/[C:24]([C:25]([F:27])([F:26])[F:28])([OH:29])[C:30]([F:33])([F:32])[F:31])=[CH:17][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 20636349(e)-6-{5-[3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenoxymethyl]-2-thienyl}-1,1,1-trifluoro-2-trifluoromethyloct-5-en-3-yn-2-olHCID 21226445Aluminium lithium hydride

Product 1

HCID 88011818HCID 88011818, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

1 g (1.3 mmol) of (E)-6-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}-1,1,1,-trifluoro-2-trifluoromethyloct-5-en-3-yn-2-ol is dissolved in 10 mL of THF and then added to a suspension of 160 mg (4.2 mmol) of lithium aluminium hydride and 450 mg (8.4 mmol) of sodium methoxide in 20 mL of THF. After stirring at reflux for 2 hours, the medium is cooled and then treated with 200 μL of water, 200 μL of 15% sodium hydroxide and 600 μL of water. After filtration, the residue is purified by chromatography on silica gel (eluent: 95 heptane/5 ethyl acetate). The desired product is obtained in the form of a yellow oil (210 mg).

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturethe medium is cooled
  3. filtrationAfter filtration
  4. customthe residue is purified by chromatography on silica gel (eluent: 95 heptane/5 ethyl acetate)

Sources & evidence

ORD record
ord-c7c05af2aecd4fb98518f03bcdbd2511
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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