Trimethylsilylacetylene → 6-Fluoronaphthalen-2-ol

HRID 1066363Notes

Reaction equation

HRID 1066363 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].C[Si]([C:20]#[CH:21])(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[CH:8]=[C:9]([OH:10])[CH:21]=[CH:20]2

Participants

5

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 37449884-Fluorophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 211987116-Fluoronaphthalen-2-olYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 2-(4-fluorophenyl)acetyl chloride (5.0g; 29 mmol) in CH2Cl2 was added to AlCl3 (7.73g;58 mmol) in CH2Cl2 at −20° C. over 30 min. Trimethylsilyl acetylene (9.96g; 101.43 mmol) was added also over 30 min and stirred at −10° C. for 1h. The mixture was poured in ice and extracted with EtOAc. The organic phase was washed with water, NaHCO3 and brine. After purification by gel silica chromatography (10% EtOAc in hexane) 2.43 g (36%) of 3-(trimethylsilyl)-6-chloro-2-naphthol was collected. The desylilation was done with TFA in CH2Cl2 at rt overnight. Purification by gel silica chromatography (10% EtOAc in hexane) afforded the title compound in 69% yield.

Workup

  1. additionThe mixture was poured in ice
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water, NaHCO3 and brine
  4. customAfter purification by gel silica chromatography (10% EtOAc in hexane) 2.43 g (36%) of 3-(trimethylsilyl)-6-chloro-2-naphthol
  5. customwas collected
  6. waitThe desylilation was done with TFA in CH2Cl2 at rt overnight
  7. customPurification by gel silica chromatography (10% EtOAc in hexane)

Sources & evidence

ORD record
ord-542f94597c134b62832c0eec0b25e2dc
Source dataset
uspto-grants-2001_06
Patent number
US06242493B1

Reaction notes

Loading…