Dichloromethane → HCID 86587081, compound

HRID 1244738Notes

Reaction equation

HRID 1244738 reaction equation
[CH2:1]([Cl:3])Cl.[Li]CCCC.C[B:10]([OH:12])[OH:11].[OH:13][C:14]([C:17]([OH:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1COCC1>[Cl:3][CH:1]([B:10]([OH:12])[OH:11])[CH3:14].[OH:13][C:14]([C:17]([OH:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 86587082HCID 86587082, compoundHCID 178418339Butyllithium

Product 1

HCID 86587081HCID 86587081, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-100 °C

Procedure

A 250 mL round bottom flask is charged with THF (60 mL) and CH2Cl2 (2.63 mL, 41.0 mmol). The solution was cooled to −100° C. with a liquid nitrogen/methanol/H2O bath. n-BuLi (1.6 N in hexanes, 25.7 mL) was added slowly over the course of 1 h. The resulting solution was stirred for an additional 45 min at −100° C. Pinacol methyl boronate, dissolved in THF (40 mL), was added and the solution was stirred overnight while warming to room temperature. The THF was removed by evaporation and hexanes (100 mL) were added. The resulting precipitate was filtered and the solution concentrated. The residue was distilled at 70° C., 2 mm Hg to yield 2.06 g (30%) of a clear colorless oil. 1H-NMR (CDCl3) δ 3.49 (q, 1H), 1.52 (d, 4H), 1.27 (s, 12H).

Workup

  1. additionwas added
  2. stirringthe solution was stirred overnight
  3. temperaturewhile warming to room temperature
  4. customThe THF was removed by evaporation and hexanes (100 mL)
  5. additionwere added
  6. filtrationThe resulting precipitate was filtered
  7. concentrationthe solution concentrated
  8. distillationThe residue was distilled at 70° C.

Sources & evidence

ORD record
ord-437f6bb76fe84b73a1f8d178a4fbd0d2
Source dataset
uspto-grants-2006_10
Patent number
US07122627B2

Reaction notes

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