Propanal → HCID 66730367, compound

HRID 1802835Notes

Reaction equation

HRID 1802835 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][C:6]([CH3:9])([OH:8])[CH:5]([OH:10])[CH:4]2[C:11]([CH3:17])([CH3:16])[CH:12]3[CH2:15][C:3]12[CH2:14][CH2:13]3.[CH:19](=O)[CH2:20][CH3:21].[Br-].[Li+].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:20]([CH:21]1[O:10][CH:5]2[C:6]([CH3:9])([CH2:7][C:2]([CH3:18])([CH3:1])[C:3]34[CH2:15][CH:12]([CH2:13][CH2:14]3)[C:11]([CH3:17])([CH3:16])[CH:4]42)[O:8]1)[CH3:19]

Participants

7

Reactant 5

HCID 527PropanalHCID 6101p-Toluenesulfonic acidHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 66731141HCID 66731141, compound

Product 1

HCID 66730367HCID 66730367, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2,4,7,7-pentamethyltricyclo[6.2.1.01.6]undecane-4,5-diol (5b, 1.7 g, 6.6 mmol), propionaldehyde (2.0 g, 33 mmol), lithium bromide (75 mg) and p-toluenesulfonic acid (75 mg) in THF (30 ml) was stirred at r. t. for 1 h, then poured onto saturated aqueous sodium bicarbonate solution (50 ml) and extracted with MTBE (2×50 ml). The combined organic phases were washed with water (2×50 ml), dried (Na2SO4), concentrated in vacuo and the residue (1.9 g) purified by flash chromatography (MTBE/hexane 1:20) and bulb-to-bulb distillation to give 6-ethyl-2,2,4,10,10-pentamethyl-5,7-dioxatetracyclo[9.2.1.01.9,04.8]tetradecane (Ib, 2+98% mixture of isomeric pairs of enantiomers, 0.83 g, 42% yield, colourless oil).

Workup

  1. extractionextracted with MTBE (2×50 ml)
  2. washThe combined organic phases were washed with water (2×50 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. distillationthe residue (1.9 g) purified by flash chromatography (MTBE/hexane 1:20) and bulb-to-bulb distillation

Sources & evidence

ORD record
ord-ead0deea0fb84cc182ce97c0352910fd
Source dataset
uspto-grants-2013_01
Patent number
US08349890B2

Reaction notes

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