Boron trifluoride etherate → Diisopropylether ethyl acetate

HRID 982281Notes

Reaction equation

HRID 982281 reaction equation
[CH2:1](SC1C=C[C:7]([C:10]2[O:11][CH:12]([C:17]3C=CC=CC=3)C(O)CN=2)=CC=1)C.CN(C)C1C=C[C:28]([C:31]2[O:32][CH:33]([C:38]3C=CC=CC=3)[CH:34](O)CN=2)=CC=1.[O:45]1[CH:60]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:46]1[CH2:47][NH:48][C:49](=[O:59])[C:50]1[CH:55]=[CH:54][C:53]([S:56][CH2:57][CH3:58])=[CH:52][CH:51]=1.B(F)(F)F.CCOCC>ClCCl>[C:10]([O:11][CH2:12][CH3:17])(=[O:32])[CH3:7].[CH:33]([O:32][CH:31]([CH3:28])[CH3:1])([CH3:34])[CH3:38].[CH2:57]([S:56][C:53]1[CH:54]=[CH:55][C:50]([C:49]2[O:59][CH:60]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[CH:46]([OH:45])[CH2:47][N:48]=2)=[CH:51][CH:52]=1)[CH3:58]

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 14650624HCID 14650624, compoundHCID 20069307HCID 20069307, compoundHCID 67928883HCID 67928883, compound

Product 2

HCID 22281796Diisopropylether ethyl acetateHCID 67928883HCID 67928883, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5RS, 6SR)-2-[4-(Ethylthio)phenyl]-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol may be prepared in the following manner: working as in Example 38 for the preparation of 2-[4-(dimethylamino)phenyl]-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol, but starting with N-[(2RS, 3RS)-2,3-epoxy-3-phenylpropyl]-4-(ethylthio)benzamide (10 g) and boron trifluoride etherate (4.3 cc) in dichloromethane (100 cc), and after crystallization of the residue obtained in an ethyl acetate/diisopropyl ether mixture (30:70 by volume), (5RS, 6SR)-2-[4-(ethylthio)phenyl]-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (4.2 g), m.p. 120° C., is obtained.

Workup

  1. customafter crystallization of the residue

Sources & evidence

ORD record
ord-e9235058c9584635b55c7a5db0f47f87
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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