Aluminium lithium hydride → HCID 118415310, compound

HRID 2201396Notes

Reaction equation

HRID 2201396 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]([OH:21])[C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=1)[O:8][C:7]([CH3:23])([CH3:22])[CH:6]=[CH:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]([OH:21])/[CH:13]=[CH:14]/[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:11]=1)[O:8][C:7]([CH3:23])([CH3:22])[CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90081634HCID 90081634, compound

Product 1

HCID 118415310HCID 118415310, compoundYield 99.4%

Procedure

To a 10 mL round bottomed flask containing 100 mg (0.271 mmol, 1 equiv.) 1-(6-bromo-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-yn-1-ol dissolved in 1.5 mL dry THP was added 12 mg (0.33 mmol, 1.2 equiv.) LiAlH4. The reaction was heated to reflux for 1 hr and cooled to ambient temperature. The reaction was quenched by addition of H2O followed by 15% NaOH (aq.) and then EtOAc. The organic layer was separated and then filtered through a short silica gel plug before being concentrated to yield 100 mg (99%) of the desired product (5) as a yellow oil. See Compound 6, FIG. 12F.

Workup

  1. dissolutiondissolved in 1.5 mL
  2. customdry THP
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 1 hr
  5. customThe reaction was quenched by addition of H2O
  6. customThe organic layer was separated
  7. filtrationfiltered through a short silica gel plug
  8. concentrationbefore being concentrated

Sources & evidence

ORD record
ord-7af308f564af4f1e95c247e85465dec0
Source dataset
uspto-grants-2016_06
Patent number
US09364460B2

Reaction notes

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