Dichloromethane → HCID 86747610, compound

HRID 1975638Notes

Reaction equation

HRID 1975638 reaction equation
[CH2:1]([Cl:3])Cl.[CH2:4]([Li])[CH2:5][CH2:6]C.[C:9]12([OH:20])[CH2:17][CH:13]([C:14]1([CH3:16])[CH3:15])[CH2:12][CH2:11][C:10]2([OH:19])[CH3:18].COCCC[B:26]([O-:28])[O-:27]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[C:9]12([OH:20])[CH2:17][CH:13]([C:14]1([CH3:16])[CH3:15])[CH2:12][CH2:11][C:10]2([OH:19])[CH3:18].[Cl:3][C@@H:1]([B:26]([O-:28])[O-:27])[CH2:4][CH2:5][CH2:6][O:20][CH3:9]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 86747608HCID 86747608, compoundHCID 178418339Butyllithium

Product 1

HCID 86747610HCID 86747610, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-100 °C

Procedure

The desired (+)-pinanediol-(S)-1-chloro-4-methoxy-butane-1-boronate is prepared according to the procedure given in Organometallics 3, 1284 (1984). Therefore methylenechloride (2.2 ml) in THF is cooled to -100° C. and n-butyllithium (13.8 ml 1.6M solution, 22.0 mMol) is added over 20 min. After 15 min at -100° C., a solution of (+)-pinanediol-3-methoxy-propane-1-boronate (5.04 g, 20 mMol) in THF is added followed by anhydrous ZnCl2 (1.42 g, 10.0 mMol). After additional 15 min at -100° C. the reaction mixture is warmed to room temperature and stirred for 2 hr at this temperature. The solvent is removed in vacuo, the residue is diluted with ether and washed with water. The organic layer is dried over Na2SO4 and is concentrated to give an oil which is purified by flash chromatography (9:1 hexane/EtOAc) to give the desired (+)-pinanediol-(S)-1-chloro-4-methoxy-butane-1-boronate as a colourless oil.

Workup

  1. customThe desired (+)-pinanediol-(S)-1-chloro-4-methoxy-butane-1-boronate is prepared
  2. customThe solvent is removed in vacuo
  3. additionthe residue is diluted with ether
  4. washwashed with water
  5. dry with materialThe organic layer is dried over Na2SO4
  6. concentrationis concentrated
  7. customto give an oil which
  8. customis purified by flash chromatography (9:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-ecf787d4c3824792b082a17184eece74
Source dataset
uspto-grants-1994_02
Patent number
US05288707

Reaction notes

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