Hydrochloric Acid → HCID 22340553, compound

HRID 585181Notes

Reaction equation

HRID 585181 reaction equation
CN(C)C(=O)O[C:5]1[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:8][CH:9]=1.[Li][CH2:25]CCC.CCCCCC.Br[C:36]1([CH:43]=[CH:42][CH:41]=[CH:40][CH2:39]1)[CH:37]=[CH2:38].Cl>CCOCC>[C:10]1([C:7]2[S:8][C:9]3[CH2:38][C:37]([C:36]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:25][C:5]=3[C:6]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21877402HCID 21877402, compoundHCID 69638377HCID 69638377, compoundHCID 178418339Butyllithium

Product 1

HCID 22340553HCID 22340553, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

30.7 g (100 mmol) of 2,3-diphenyl-thienylcarbonic acid dimethylamide was mixed with 100 ml ether and the resulting suspension was added in some portions at 0° C. to solution of 1-stiryllitium prepared from 62 ml 1.6M BuLi in hexane (100 mmol) and 27 g 1-bromostyrene (150 mmol) in 200 ml ether. The mixture warmed to room temperature (r.t.) and was stirred for 1 h. The resulting solution was poured into 500 ml of 5% aqueous HCl. The organic phase was collected, separated from insoluble impurities, washed with water, dried over MgSO4 and evaporated to give 20.9 g (57%) of crystalline solid. The product can be contaminated with 5-10% of starting amide (by NMR) and can be used without further purification.

Workup

  1. additionthe resulting suspension was added in some portions at 0° C. to solution of 1-stiryllitium
  2. customThe organic phase was collected
  3. customseparated from insoluble impurities
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-5d89521f95c94f3f84500b7ffe5772af
Source dataset
uspto-grants-2005_08
Patent number
US06930190B2

Reaction notes

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