Tetrahydrofuran → HCID 18355592, compound

HRID 429445Notes

Reaction equation

HRID 429445 reaction equation
C([Li])CCC.O1CCCC1.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CN(C)[C:28](=[O:39])[C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=1[O:37][CH3:38]>Cl>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:28]([C:29]2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=2[O:37][CH3:38])=[O:39])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 13513547HCID 13513547, compoundHCID 178418339Butyllithium

Product 1

HCID 18355592HCID 18355592, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Butyllithium (2.0M in hexanes, 6.6 ml, 13.2 mmol) was added dropwise under nitrogen, at −78° C. to a stirred tetrahydrofuran (20 ml) solution of 4-benzyloxy-bromobenzene (3.15 g, 11.97 mmol) to give a yellow coloured suspension, which was stirred for 10 minutes. A tetrahydrofuran (10 ml) solution of N,N-dimethyl 2,5-dimethoxybenzamide (2.09 g, 9.99 mmol) was then added slowly, and the resulting mixture warmed to room temperature over 20 h. The mixture was diluted with 50ml of 1M hydrochloric acid and the product extracted into dichloromethane (4×50 ml). The combined extracts were washed with brine, dried over sodium sulfate and evaporated to a yellow coloured solid. This crude product was purified by column chromatography on silica gel 60, using 4:1 petrol/ethyl acetate as the eluent. This gave the product as a colourless solid, which was recrystallised from hot ethanol (25 ml) to give the product as colourless platelets which were vacuum dried.

Workup

  1. customto give a yellow coloured suspension, which
  2. extractionthe product extracted into dichloromethane (4×50 ml)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to a yellow coloured solid
  6. customThis crude product was purified by column chromatography on silica gel 60

Sources & evidence

ORD record
ord-744affa300544124bc80beac4d5b60be
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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