(6S,7S)-5,6,7,8-Tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarboxaldehyde → HCID 117666316, compound

HRID 523344Notes

Reaction equation

HRID 523344 reaction equation
[CH3:1][C:2]1[C:3]([CH:18]=[O:19])=[CH:4][C:5]2[C:6]([CH3:17])([CH3:16])[C@@H:7]([CH3:15])[C@H:8]([CH3:14])[C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.O1CCCC1>[CH3:1][C:2]1[C:3]([CH2:18][OH:19])=[CH:4][C:5]2[C:6]([CH3:17])([CH3:16])[C@@H:7]([CH3:15])[C@H:8]([CH3:14])[C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 11459584(6S,7S)-5,6,7,8-Tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarboxaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 117666316HCID 117666316, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.00 g (38.7 mmol) of (6S,7S)-3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde in ether (50 ml) and tetrahydrofuran (THF, 15 ml) was added dropwise during 45 min to a suspension of LiAlH4 (1.48 g, 39.0 mmol) in ether (55 ml) at 0° C. The reaction mixture was left warming up to room temperature and then heated to reflux for 1.5 h. After cooling to room temperature, the remaining LiAlH4 was quenched with water (2 ml) and NaOH (10%, 2 ml) and water (6 ml) was added. The formation of a white precipitate was observed which was filtered off. Ether was added and the organic phase washed with water, dried (Na2SO4) and concentrated to give 10.11 g (quant.) of the product.

Workup

  1. waitThe reaction mixture was left
  2. temperatureheated
  3. temperatureto reflux for 1.5 h
  4. temperatureAfter cooling to room temperature
  5. customthe remaining LiAlH4 was quenched with water (2 ml) and NaOH (10%, 2 ml) and water (6 ml)
  6. additionwas added
  7. filtrationwas filtered off
  8. additionEther was added
  9. washthe organic phase washed with water
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customto give 10.11 g (quant.) of the product

Sources & evidence

ORD record
ord-8b08a074487a4d2e8961b91331560f2e
Source dataset
uspto-grants-2016_05
Patent number
US09334464B2

Reaction notes

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