Triethylsilane → HCID 90310561, compound

HRID 1519149Notes

Reaction equation

HRID 1519149 reaction equation
[F:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:8]2(O)[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[O:13][CH3:14])[CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 90310642HCID 90310642, compound

Product 1

HCID 90310561HCID 90310561, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 3-L round-bottom flask were added a stir bar, 1-(3-fluoro-2-methoxyphenyl)-cyclobutanol (80.17 g, 410 mmol), dry DCM (1231 mL), Et3SiH (200 mL, 1.23 mol) and TFA (93 mL, 1.2 mmol). The resultant mixture was stirred at rt for 22 h before concentrating to dryness and subjecting the residue to FCC to give 1-cyclobutyl-3-fluoro-2-methoxybenzene as a pale-yellow oil (51.90 g, 70.5%). 1HNMR (400 MHz, CDCl3) δ 7.07-6.93 (m, 3H), 3.91 (s, 3H), 3.85-3.81 (m, 1H), 2.40-2.36 (m, 2H), 2.20-2.07 (m, 3H), 1.91-1.88 (m, 1H).

Workup

  1. additionTo a 3-L round-bottom flask were added a stir bar
  2. concentrationbefore concentrating to dryness

Sources & evidence

ORD record
ord-d82889b2eef54f3dbdc560839db328ae
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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