Methanol → HCID 57887345, compound

HRID 1819544Notes

Reaction equation

HRID 1819544 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][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:15][CH:16]=2)[O:11][C:10]=1[C:38]1[CH:43]=[C:42]([O:44]C)[C:41]([O:46]CC2C=CC=CC=2)=[C:40]([O:54]C)[CH:39]=1)C1C=CC=CC=1.B(Br)(Br)Br.CO.O>ClCCl>[OH:8][C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:15][CH:16]=2)[O:11][C:10]=1[C:38]1[CH:43]=[C:42]([OH:44])[C:41]([OH:46])=[C:40]([OH:54])[CH:39]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 57887350HCID 57887350, compound

Product 1

HCID 57887345HCID 57887345, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 40j (0.455 g, 0.6 mmol) in dichloromethane (25 ml) under Ar at 0° C. was added boron tribromide in dichloromethane (1.0M, 6 ml, 6 mmol, 9.8 equ). The mixture was warmed to room temperature and then stirred for 22 hours. The reaction was then cooled to 0° C. and methanol (25 ml) added. The reaction was heated to reflux for 2 hours, then concentrated in vacuo to give a yellow solid. Water (50 ml) was added and sonicated then left to stand overnight then 9j (0.325 g, 99%) was collected as a yellow solid.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2 hours
  4. concentrationconcentrated in vacuo
  5. customto give a yellow solid
  6. customsonicated
  7. waitthen left
  8. waitto stand overnight
  9. custom9j (0.325 g, 99%) was collected as a yellow solid

Sources & evidence

ORD record
ord-8d057f55fa2245958eb884b19eed00f7
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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