Allyl bromide → HCID 10762606, compound

HRID 1377959Notes

Reaction equation

HRID 1377959 reaction equation
[H-].[Na+].[C:3]1([C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:10][CH2:11][C@@H:12]([OH:16])[CH2:13][CH:14]=[CH2:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:29](Br)[CH:30]=[CH2:31].[Cl-].[NH4+]>C1COCC1>[CH2:31]([O:16][C@@H:12]([CH2:13][CH:14]=[CH2:15])[CH2:11][O:10][C:9]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH:30]=[CH2:29]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 107836644-Penten-2-ol, 1-(triphenylmethoxy)-, (2S)-

Product 1

HCID 10762606HCID 10762606, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

A 60% suspension of sodium hydride in mineral oil (268.9 g, 6.72 mole, 1.5 eq.) was suspended in 2.8 L of dry THF under N2 and a solution (S)-1-(triphenylmethoxy)-4-penten-2-ol (1543 g, 4.48 mole) in 5.6 L of dry THF was added at room temperature. The resultant mixture was stirred at room temperature for 1.5 hours and then 770 mL (8.89 mole, 2.0 eq.) of freshly distilled allyl bromide was added over 20 minutes. The reaction was heated to 45° C. for 1-2 hours. The reaction mixture was cooled to 15°-20° C. and 2 L of an aqueous saturated solution of ammonium chloride was slowly added to quench the excess base. The resultant mixture was diluted with 1 L of ethyl acetate and 1 L of water and the organic layer was isolated. The aqueous layer was back-extracted with 500 mL of ethyl acetate and the combined organic layers were dried (MgSO4) and evaporated in vacuo to give 1867 g (98%) of (S) -1,1',1"-[[[2-(2-propenyloxy) -4-pentenyl]oxy]methylidyne]tris [benzene] as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to 15°-20° C.
  2. customto quench the excess base
  3. additionThe resultant mixture was diluted with 1 L of ethyl acetate and 1 L of water
  4. customthe organic layer was isolated
  5. extractionThe aqueous layer was back-extracted with 500 mL of ethyl acetate
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-7d2fff2cf84645d28996403096a72e56
Source dataset
uspto-grants-1997_09
Patent number
US05665877

Reaction notes

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