Triethylamine → HCID 68415588, compound

HRID 220236Notes

Reaction equation

HRID 220236 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:15]1[CH2:25][C:23](=O)[C:22]2[C:17](=[CH:18][CH:19]=CC=2)[CH2:16]1.[C:26]1(=[O:32])[CH2:31][CH2:30][CH2:29][CH:28]=[CH:27]1.FC(F)(F)S(O)(=O)=O.[CH3:41][CH2:42]N(CC)CC>>[O:32]=[C:26]1[CH:31]2[CH2:41][CH2:42][CH:28]([C:29]3[CH2:19][CH2:18][C:17]4[C:22]([C:30]=32)=[CH:23][CH:25]=[CH:15][CH:16]=4)[CH2:27]1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 107241-TetraloneHCID 135942-Cyclohexen-1-oneHCID 14812Phosphorus oxide (P4O10)HCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 68415588HCID 68415588, compound

Procedure

To a suspension of 1.9 g of phosphorous pentoxide in 50 mL DCManh. were added 4.5 mL of alpha tetralone followed by 9.9 mL of 2-cyclohexen-1-one at rt. The suspension was cooled to 0° C. with an ice bath before 9.0 mL of trifluoromethanesulfonic acid was carefully added. The reaction mixture was warmed to rt and then heated at 40° C. overnight. 18.5 mL of NEt3 were dropwise added at 0° C., the mixture was stirred at rt for 10 min and then evaporated to dryness. Purification by CC with EtOAc-Hept (2:8) yielded 3.9 g of rac-(1R*,4R*)-1,2,3,4,9,10-hexahydro-3-oxo-1,4-ethanophenanthrene as yellow oil.

Workup

  1. additionwas carefully added
  2. temperatureheated at 40° C. overnight
  3. customevaporated to dryness
  4. customPurification by CC with EtOAc-Hept (2:8)

Sources & evidence

ORD record
ord-b5540379118f463eb03ef92bdc71acc3
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

Loading…