Diethyl Sulfate → HCID 10171332, compound

HRID 495116Notes

Reaction equation

HRID 495116 reaction equation
C(OC[C:5]1([CH3:16])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1([CH3:15])[CH3:14])C.C[CH:18]1C(C)(C)C2C(=CC=CC=2)[CH:19]1[OH:29].[H-].[Na+].S(OCC)(OCC)(=O)=O>>[CH2:19]([O:29][CH:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH3:14])([CH3:15])[CH:5]1[CH3:16])[CH3:18]

Participants

5

Reactant 4

HCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 10171362HCID 10171362, compoundHCID 12113148HCID 12113148, compound

Product 1

HCID 10171332HCID 10171332, compoundYield 45%

Procedure

The protocol described for 2-Ethoxymethyl-1,1,2-trimethylindan (Example 3) was repeated with 2,3,3-Trimethylindan-1-ol (1.76 g, 10 mmol), NaH (870 mg at 55%, 20 mmol, 2 equiv.) and diethyl sulphate (3.08 g, 20 mmol, 2 equiv.). The crude product obtained was purified by column chromatography on SiO2 (hexane/MTBE 19:1) followed by a bulb-to-bulb distillation at 0.15 mbar/80° C. to obtain the product as a colourless liquid in 45% yield. Only the major 1,2-trans isomer was isolated and characterised.

Workup

  1. customThe crude product obtained
  2. customwas purified by column chromatography on SiO2 (hexane/MTBE 19:1)
  3. distillationfollowed by a bulb-to-bulb distillation at 0.15 mbar/80° C.

Sources & evidence

ORD record
ord-2ad98136700548f7b5adc43932159ac7
Source dataset
uspto-grants-2009_05
Patent number
US07538243B2

Reaction notes

Loading…