Boron trifluoride etherate → HCID 9921313, compound

HRID 2351464Notes

Reaction equation

HRID 2351464 reaction equation
C([O:8][NH:9][CH:10]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:14]=2[CH:13]=1)[CH3:11])C1C=CC=CC=1.C([Li])CCC.FC1C=CC2SC=CC=2C=1.B(F)(F)F.CC[O:43][CH2:44]C.[NH4+:46].[Cl-]>C1COCC1>[OH:8][N:9]([CH:10]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:14]=2[CH:13]=1)[CH3:11])[C:44]([NH2:46])=[O:43]

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherateHCID 25517Ammonium ChlorideHCID 118159505-Fluoro-1-benzothiopheneHCID 86743433HCID 86743433, compoundHCID 178418339Butyllithium

Product 1

HCID 9921313HCID 9921313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-benzyloxy-1-(5-fluorobenzo[b]thien-2-yl)ethyl amine. n-Butyl lithium (2.5M in hexanes, 4.4 mL) was added to a solution of 5-fluorobenzothiophene, prepared as described in part a, above (1.52 g, 10 mmole) in THF (25 mL) at -78° C. After stirring for 30 minutes borontrifluoride etherate was added followed by O-benzyl acetaldehyde oxime. Fifteen minutes later aqueous NH4Cl was added and the reaction warmed to room temperature. The aqueous phase was extracted twice with ether and the combined organic layers washed twice with brine, dried over MgSO4 and concentrated. The desired product was obtained as a yellow oil (2.9 g).

Workup

  1. customprepared
  2. customat -78° C
  3. additionwas added
  4. extractionThe aqueous phase was extracted twice with ether
  5. washthe combined organic layers washed twice with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b6fe6769f5d54892a02c1d3b8661e4f8
Source dataset
uspto-grants-1989_10
Patent number
US04873259

Reaction notes

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