Formaldehyde → HCID 15701917, compound

HRID 1030308Notes

Reaction equation

HRID 1030308 reaction equation
[C:1]1([C@@H:11]([NH:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:19]=[O:20]>C(O)CCC>[C:1]1([C@@H:11]([N:13]([CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])[CH2:19][O:20][CH2:10][CH2:1][CH2:2][CH3:3])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 15701914HCID 15701914, compound

Product 1

HCID 15701917HCID 15701917, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The title compound was prepared from (S)-(-)-N-1-(1-naphthyl)ethyl-N-trimethylsilylmethylamine by reaction with n-butanol and aqueous formaldehyde following the procedure of Example 2 to give the crude acetal (80% pure) as a pale yellow oil (5.5 g, 82%). δH [CD3)2CO] 0.1 (s, SiMe3), 0.93 (t, J 7 Hz, CH3CH2), 1.2-1.7 (m, CH3CH and (CH2)2), 2.22, 2.45 (AB quartet, J 15 Hz, NCH2Si), 3.25 (t, J 7 Hz, CH2O), 4.22, 4.35 (AB quartet, J 10 Hz, NCH2O), 4.78 (q, J 7 Hz, CH), 7.3-8.5 (m, naphthyl).

Sources & evidence

ORD record
ord-b84ebc8f405b41daa8465b2a341dab85
Source dataset
uspto-grants-1992_04
Patent number
US05104989

Reaction notes

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