Methanol → HCID 10006037, compound

HRID 1819551Notes

Reaction equation

HRID 1819551 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]([CH3:34])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:33])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:15][CH:16]=2)[O:11][C:10]=1[C:35]1[CH:40]=[C:39]([O:41]C)[C:38]([O:43]C)=[C:37]([O:45]C)[CH:36]=1)C1C=CC=CC=1.B(Br)(Br)Br.CO>ClCCl>[OH:8][C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([CH2:20][CH2:21][CH:22]([CH3:34])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:33])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:31])[CH3:32])=[CH:15][CH:16]=2)[O:11][C:10]=1[C:35]1[CH:40]=[C:39]([OH:41])[C:38]([OH:43])=[C:37]([OH:45])[CH:36]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 68887960HCID 68887960, compound

Product 1

HCID 10006037HCID 10006037, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 48 (0.048 g, 0.08 mmol) in dichloromethane (2.5 ml) under argon at 0° C. was added boron tribromide (1.0M in DCM, 2.5 ml, 26 eq). The reaction was then warmed to room temperature and stirred for 19 hours. The mixture was then cooled to 0° C., methanol (2 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, chloroform:methanol, 9:1) to give 9i* (0.033g, 87%) as a waxy 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, chloroform:methanol, 9:1)
  8. customto give 9i* (0.033g, 87%) as a waxy solid

Sources & evidence

ORD record
ord-412b70c8edad4809986569ac71a0ffd9
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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