Methanol → HCID 9888699, compound

HRID 1819547Notes

Reaction equation

HRID 1819547 reaction equation
C([O:8][C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([CH2:20][CH2:21][CH:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:15][CH:16]=2)[O:11][C:10]=1[C:30]1[CH:35]=[C:34]([O:36]C)[C:33]([O:38]CC2C=CC=CC=2)=[C:32]([O:46]C)[CH:31]=1)C1C=CC=CC=1.B(Br)(Br)Br.CO>ClCCl>[CH3:29][CH:22]([CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:21][CH2:20][C:14]1[CH:13]=[C:12]2[C:17]([C:18](=[O:19])[C:9]([OH:8])=[C:10]([C:30]3[CH:35]=[C:34]([OH:36])[C:33]([OH:38])=[C:32]([OH:46])[CH:31]=3)[O:11]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 57887324HCID 57887324, compound

Product 1

HCID 9888699HCID 9888699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 47 (0.028 g, 0.05 mmol) in dichloromethane (1 ml) under argon at 0° C. was added boron tribromide (1.0M in DCM, 0.7 ml, 14 eq). The reaction was then warmed to room temperature and stirred for 23 hours. The mixture was then cooled to 0° C., methanol (1 ml) added heated to reflux for 2 hours. The reaction was then cooled and concentrated in vacuo to give a solid that was chromatographed (silica gel, DCM:methanol, 19:1) to give 9g* (0.008g, 37%) as a yellow solid.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. temperatureheated
  3. temperatureto reflux for 2 hours
  4. temperatureThe reaction was then cooled
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. customthat was chromatographed (silica gel, DCM:methanol, 19:1)
  8. customto give 9g* (0.008g, 37%) as a yellow solid

Sources & evidence

ORD record
ord-420a7dbdf6ae4a009b552623cbb47981
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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