Lithium → HCID 59386493, compound

HRID 2357701Notes

Reaction equation

HRID 2357701 reaction equation
[Li].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[Br-].[OH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:28][CH:27]=1>C(O)C>[OH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:13]/[C:12]2[CH:15]=[CH:16][C:9]([O:8][CH:3]3[CH2:4][CH2:5][CH2:6][CH2:7][O:2]3)=[CH:10][CH:11]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 3028194LithiumHCID 112527364-(2-Tetrahydro-2H-pyranoxy)benzaldehydeHCID 21924204HCID 21924204, compound

Product 1

HCID 59386493HCID 59386493, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.23 g of lithium was dissolved in 150 ml of ethanol. Then 6.2 g of 4-(tetrahydropyran-2-yloxy)benzaldehyde (H) was added. The solution was cooled in an ice-water bath and 16.5 g of 4-(6-hydroxyhexyloxy)phenylmethyltriphenylphosphonium bromide (I) was added. After stirring for 2 hours at room temperature, a white precipitate was obtained. 3.34 g of (E)-4-(6-hydroxyhexyloxy)-4′-(tetrahydropyran-2-yloxy)stilbene (J, 31%) was obtained after collection by filtration and two washings with 150 ml of ethanol.

Workup

  1. temperatureThe solution was cooled in an ice-water bath
  2. customa white precipitate was obtained

Sources & evidence

ORD record
ord-e74a3f8915c74c75aeffabce51235469
Source dataset
uspto-grants-2010_07
Patent number
US07763330B2

Reaction notes

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