Hydrochloric Acid → HCID 3536730, compound

HRID 2292419Notes

Reaction equation

HRID 2292419 reaction equation
C([Li])CCC.[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.Cl>C1COCC1>[CH2:14]([C:8]1[CH:9]=[CH:10][C:11]([B:19]([OH:24])[OH:20])=[C:12]([F:13])[C:7]=1[F:6])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 14495798HCID 14495798, compoundHCID 178418339Butyllithium

Product 1

HCID 3536730HCID 3536730, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (10 cm3, 10M in hexanes, 0.1 mol) was added dropwise to a stirred, cooled (-78° C.) solution of the compound from Example 22 (17.3 g, 94 m mol) in dry THF (250 cm3) under an atmosphere of dry nitrogen. The reaction mixture was stirred (2.5 h) then a previously cooled (-78° C.) solution of triisopropyl borate (35.7 g, 0.19 mol) in dry THF (70 cm3) added dropwise at -78° C. The reaction mixture was allowed to warm to room temperature overnight then stirred (1h) with hydrochloric acid (10%, 100 cm3). The product was extracted into diethyl ether (2×100 cm3), and the combined extracts washed with water and dried (MgSO4). The solvent was removed in vacuo to yield colourless crystals.

Workup

  1. additionadded dropwise at -78° C
  2. extractionThe product was extracted into diethyl ether (2×100 cm3)
  3. washthe combined extracts washed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customto yield colourless crystals

Sources & evidence

ORD record
ord-35e4607dc1de4831bacb558486bcea6f
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

Loading…