Aluminium lithium hydride → HCID 69442579, compound

HRID 446163Notes

Reaction equation

HRID 446163 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[C:14]([CH:16]=[O:17])[S:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[C:14]([CH2:16][OH:17])[S:15][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 85708562HCID 85708562, compound

Product 1

HCID 69442579HCID 69442579, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-benzyloxy-benzothiophene-2-carbaldehyde (described by Nomura Y., WO 9635688 A1, 6.50 g, 24.20 mmol) in THF (50 ml) was added dropwise to a −30° C. cooled suspension of LiAlH4 (0.85 g, 22.26 mmol). After warming up to room temperature the mixture was stirred overnight, cooled to −10° C., hydrolyzed with ice water, extracted with dichloromethane, dried over Na2SO4, filtered and concentrated under vacuum to give the crude product. Flash chromatography on silica gel (toluene/ethyl acetate: 7/3) yielded a limpid oil (4.50 g, 69%).

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give the crude product

Sources & evidence

ORD record
ord-be0c00ed033c4a78b64f907af44d2ca8
Source dataset
uspto-grants-2013_07
Patent number
US08476455B2

Reaction notes

Loading…