Hydride → (2R,6R)-(+)-2,6,10-trimethylundecan-1-ol

HRID 328141Notes

Reaction equation

HRID 328141 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH3:16])[CH2:5][CH2:6][CH2:7][C@H:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-]>CCOCC>[CH3:16][C@H:4]([CH2:5][CH2:6][CH2:7][C@H:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:3][OH:2]

Participants

5

Reactant 3

HCID 166653HydrideHCID 14200217HCID 14200217, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10353213(2R,6R)-(+)-2,6,10-trimethylundecan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2(R),6(R),10-trimethylundecanoic acid methyl ester (172 mg., [α]D25 -11.30°) and lithium aluminum hydride (170 mg.) in absolute ether (20 ml.) were refluxed with stirring for 2 1/2 hours. The reaction mixture was cooled in an ice-bath and excess of hydride was destroyed by carefully adding water followed by 30 ml. of 1 N aqueous H2SO4. The aqueous phase was extracted with ether (3 × 40 ml.) and the combined ether extract was washed with water (3 × 30 ml.) and dried (MgSO4). The crude product (155 mg.) was purified by evaporative distillation to give 152 mg. (100% yield) of 2(R),6(R),10-trimethylundecan-1-ol as a colorless liquid, b.p. 100°-102° C./0.08 mm Hg.; [α]D25 + 6.09° C. (c 2.0366, hexane).

Workup

  1. customwas destroyed by carefully adding water
  2. extractionThe aqueous phase was extracted with ether (3 × 40 ml.)
  3. extractionthe combined ether extract
  4. washwas washed with water (3 × 30 ml.)
  5. dry with materialdried (MgSO4)
  6. distillationThe crude product (155 mg.) was purified by evaporative distillation
  7. customto give 152 mg

Sources & evidence

ORD record
ord-2af1b7c6efb5429cad7f97cebe661fb7
Source dataset
uspto-grants-1977_04
Patent number
US04016178

Reaction notes

Loading…