Diethyl Ether → HCID 67069050, compound

HRID 604947

Reaction equation

HRID 604947 reaction equation
CCOCC.Br[C:7]1[C:20]2[O:19][C:18]3[C:13](=[CH:14][C:15]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:16][C:17]=3Br)[C:12]([CH3:27])([CH3:26])[C:11]=2[CH:10]=[C:9]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:8]=1.[Li]CCCC.[Si:37]([Cl:41])(Cl)([CH3:39])[CH3:38]>CCCCCC>[Cl:41][Si:37]([CH3:39])([CH3:38])[C:7]1[C:20]2[O:19][C:18]3[C:13](=[CH:14][C:15]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:16][C:17]=3[Si:37]([Cl:41])([CH3:39])[CH3:38])[C:12]([CH3:27])([CH3:26])[C:11]=2[CH:10]=[C:9]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:8]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6398DichlorodimethylsilaneHCID 42212484,5-Dibromo-2,7-bis(1,1-dimethylethyl)-9,9-dimethyl-9H-xantheneHCID 178418339Butyllithium

Product 1

HCID 67069050HCID 67069050, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-65 °C

Procedure

The reaction outlined in the reaction scheme below is as follows: Et2O (125 mL) and 4,5-dibromo-2,7-di(tert-butyl)-9,9-dimethylxanthene (9.54 g, 19.9 mmol) were combined and cooled to −65° C. A hexane solution of BuLi (19.2 mL, 47.7 mmol) was added dropwise over 5 min and the colorless suspension was allowed to warm to −30° C. over a period of 45 min during which time the starting material dissolved (at about −40° C.). After 15 min at −30° C. the solution was cooled to −80° C. and cold SiMe2Cl2 (20.5 g, 159 mmol) was added in one portion.

Workup

  1. customThe reaction outlined in the reaction scheme
  2. temperatureto warm to −30° C. over a period of 45 min during which time the starting material
  3. dissolutiondissolved (at about −40° C.)
  4. temperatureAfter 15 min at −30° C. the solution was cooled to −80° C.

Sources & evidence

ORD record
ord-2483d4b7565d4f7b9bb5f328e901c76d
Source dataset
uspto-grants-2011_03
Patent number
US07910760B2

Linked notes

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