Methanol → HCID 20230675, compound

HRID 2290906Notes

Reaction equation

HRID 2290906 reaction equation
Cl.[CH2:2]([N:4]1[CH2:12][CH:11]2[CH:6]([CH2:7][CH2:8][C:9]3[C:16]([O:17]C)=[C:15]([O:19]C)[CH:14]=[CH:13][C:10]=32)[CH2:5]1)[CH3:3].B(Br)(Br)[Br:22].CO.CCOCC>C(Cl)Cl>[BrH:22].[CH2:2]([N:4]1[CH2:12][CH:11]2[CH:6]([CH2:7][CH2:8][C:9]3[C:16]([OH:17])=[C:15]([OH:19])[CH:14]=[CH:13][C:10]=32)[CH2:5]1)[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 20230764HCID 20230764, compound

Product 1

HCID 20230675HCID 20230675, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the compound of example 6 (1.1 g, 3.7 mmole) and 11 mL CH2Cl2 was stirred under N2 at -78° C. and a solution of BBr3 (1.08 mL, 11.5 mmole) in 3.5 mL CH2Cl2 was added dropwise. The reaction mixture was stirred for 1 hr at -78°, 2 hours at 0°, and 1 hour at room temperature. After cooling again to -78°, 20 mL MeOH was added dropwise. The reaction mixture was allowed to slowly warm to room temperature overnight. Approximately 20 mL Et2O was added and the precipitate filtered, washed with 5% EtOH in Et2O, and dried (in-vacuo) to yield 0.8 g pale yellow solid; M+ 233; mp 223°-7°.

Workup

  1. custom1 hour
  2. customat room temperature
  3. temperatureAfter cooling again to -78°
  4. filtrationthe precipitate filtered
  5. washwashed with 5% EtOH in Et2O
  6. customdried (in-vacuo)

Sources & evidence

ORD record
ord-7b95f2ba62d941789460df4b40be3583
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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