Sodium Hydroxide → HCID 54335688, compound

HRID 1034323Notes

Reaction equation

HRID 1034323 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>O1CCCC1>[C:8]1([S:7][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]2[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=2[CH2:23][OH:24])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 21226445Aluminium lithium hydrideHCID 85590543HCID 85590543, compound

Product 1

HCID 54335688HCID 54335688, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.292 g, 0.007 mole) in tetrahydrofuran (30 ml) is added a solution of 2-(6-thiophenoxyhexylthio)benzoic acid (2.42 g, 0.007 mole) in tetrahydrofuran (30 ml). The reaction is stirred at room temperature under argon, overnight. When the reaction is complete several drops of ice water are added followed by cold 10% sodium hydroxide (approximately 1.0 ml), followed by cold 10% sodium hydroxide (approximately 1.0 ml), followed by more ice water. This produces a dry granular precipatate which is filtered and is washed. The filtrate is then dried over magnesium sulfate, filtered and is evaporated. The crude alcohol is flash chromatographed on silica gel to give the desired compound.

Workup

  1. additionare added
  2. customThis produces a dry granular precipatate which
  3. filtrationis filtered
  4. washis washed
  5. dry with materialThe filtrate is then dried over magnesium sulfate
  6. filtrationfiltered
  7. customis evaporated
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-da7939a2978843b28f3e5a686a2e414c
Source dataset
uspto-grants-1994_05
Patent number
US05314918

Reaction notes

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