Toluene → HCID 11499533, compound

HRID 1784117Notes

Reaction equation

HRID 1784117 reaction equation
C[O:2][C:3]([C:5]12[CH2:14][CH:9]3[S:10][CH:11]([S:13][CH:7]([S:8]3)[CH2:6]1)[CH2:12]2)=O.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C>CCCCCC>[OH:2][CH2:3][C:5]12[CH2:12][CH:11]3[S:10][CH:9]([S:8][CH:7]([S:13]3)[CH2:6]1)[CH2:14]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 11572349HCID 11572349, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 11499533HCID 11499533, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A flame-dried, 25 mL round-bottomed flask equipped with a Teflon-coated magnetic bar and a septum with an argon inlet was charged with 270 mg (1.10 mmol) of 2,4,9-Trithia-tricyclo[3.3.1.13,7]decane-7-carboxylic acid methyl ester and 5 mL of dry toluene. Cooled by an ice bath, the solution was charged with 1.60 mL of 1.5 M (2.3 mmol) diisobutyl aluminum hydride in hexane. The solution was stirred at 0° C. until the complete consumption of the starting material was observed (monitored by TLC). The solution was quenched by 2 mL of methanol and allowed to warm to the ambient temperature. The filtration through a celite filter cake gave 240 mg (97%) of 7-hydroxymethyl-2,4,9-trithiaadamantane.

Workup

  1. customA flame-dried, 25 mL round-bottomed flask equipped with a Teflon-coated magnetic bar
  2. temperatureCooled by an ice bath
  3. customThe solution was quenched by 2 mL of methanol
  4. temperatureto warm to the ambient temperature
  5. filtrationThe filtration through a celite
  6. filtrationfilter cake

Sources & evidence

ORD record
ord-186682100cc14e9eb9f5399f077666f1
Source dataset
uspto-grants-2009_03
Patent number
US07501529B2

Reaction notes

Loading…