Aluminium lithium hydride → 2-(Methylamino)-4-(1-naphthyloxy)-1-butanol

HRID 66416Notes

Reaction equation

HRID 66416 reaction equation
[CH:1]([NH:3][CH:4]([CH2:7][CH2:8][O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH2:5][OH:6])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:3][CH:4]([CH2:7][CH2:8][O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 227550192-(Formylamino)-4-(1-naphthyloxy)butanol

Product 1

HCID 203721512-(Methylamino)-4-(1-naphthyloxy)-1-butanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 2-(formylamino)-4-(1-naphthyloxy)butanol (7.1 g), prepared as described in Example 3, in dry THF (150 ml) is added dropwise to a suspension of LiAlH4 (5.0 g) in THF (150 ml). The mixture is heated at 45° C. for 3 hours and cooled. Excess LiAlH4 is destroyed by the careful addition of THF/water (9:1). The mixture is filtered through diatomaceous earth (Celite). The filtrate is dried and evaporated. The residue is crystallized from diethyl ether to give the title compound, γmaxCHCl3 3650, 3352, 1595 and 1580 cm-1.

Workup

  1. temperaturecooled
  2. customExcess LiAlH4 is destroyed by the careful addition of THF/water (9:1)
  3. filtrationThe mixture is filtered through diatomaceous earth (Celite)
  4. customThe filtrate is dried
  5. customevaporated
  6. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-5a514474f3fb41b087bfd577a449aba6
Source dataset
uspto-grants-1978_12
Patent number
US04131745

Reaction notes

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