Tetrabutylammonium Fluoride → HCID 90424166, compound

HRID 1055165Notes

Reaction equation

HRID 1055165 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([Si]([O:36][CH2:37][CH:38]1[O:43][CH2:42][C:41]2=[N:44][CH:45]=[CH:46][N:40]2[CH2:39]1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>O1CCCC1>[N:44]1[CH:45]=[CH:46][N:40]2[CH2:39][CH:38]([CH2:37][OH:36])[O:43][CH2:42][C:41]=12

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90423419HCID 90423419, compound

Product 1

HCID 90424166HCID 90424166, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add tetra-N-butylammonium fluoride (1M in tetrahydrofuran; 13.98 mL; 3 equiv; 13.98 mmoles) to a solution of tert-butyl-(6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-6-ylmethoxy)-diphenyl-silane (6.96 g; 1.0 equiv; 17.73 mmoles) in tetrahydrofuran (100 mL) and stir for 1 hour. Load the solution directly onto an SCX ion-exchange column and elute with 15% methanol in dichloromethane followed by 20% ((2N ammonia in methanol) in dichloromethane) to afford (2 scx ion-exchange purifications were required) 6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-6-ylmethanol (2.59 g; 61%). MS (m/z): 155(M+1).

Workup

  1. washLoad the solution directly onto an SCX ion-exchange column and elute with 15% methanol in dichloromethane

Sources & evidence

ORD record
ord-c63e406216ff4be498b87279c9c4ca95
Source dataset
uspto-grants-2016_07
Patent number
US09394317B2

Reaction notes

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