Lithium tri-tert-butoxyaluminohydride → HCID 20271480, compound

HRID 485107Notes

Reaction equation

HRID 485107 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[C:15]([C:18](Cl)=[O:19])[CH:16]=[CH:17][C:11]=3[CH:10]=[CH:9][C:8]=2[CH:21]=1)([O-:3])=[O:2].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[C:15]([CH:18]=[O:19])[CH:16]=[CH:17][C:11]=3[CH:10]=[CH:9][C:8]=2[CH:21]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 54145385HCID 54145385, compound

Product 1

HCID 20271480HCID 20271480, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Stir a mixture of the crude 8-nitrodibenzo[b,f]thiepin-3-carboxylic acid chloride in dry tetrahydrofuran at -78° C. under nitrogen, and add dropwise a filtered solution of 1.1 equivalents of lithium tri-tertiarybutoxy-aluminum hydride in tetrahydrofuran. Stir the mixture for 30 minutes at -78° C. and allow to warm to ambient temperature. Add the mixture to ice-cold dilute hydrochloric acid, and isolate the product by extraction with chloroform. Purify the title compound by chromatography on silica gel using a mixture of ethyl acetate and toluene for elution.

Workup

  1. stirringStir the mixture for 30 minutes at -78° C.
  2. additionAdd the mixture to ice-cold dilute hydrochloric acid
  3. customisolate the product
  4. extractionby extraction with chloroform
  5. customPurify the title compound by chromatography on silica gel using
  6. additiona mixture of ethyl acetate and toluene
  7. washfor elution

Sources & evidence

ORD record
ord-b41855c415ec454ca4e61a19ab492c55
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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