Triethyl phosphite → HCID 131715563, compound

HRID 1253310Notes

Reaction equation

HRID 1253310 reaction equation
[N+:1]([C:4]1[C:9]2[CH2:10][CH:11]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:12]([C:16]([O:18][CH3:19])=[O:17])[C:13](=O)[NH:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].C[Si](C)(C)[N-][Si](C)(C)C.[K+].P(OCC)(OCC)[O:39]CC>O1CCCC1.O=O>[N+:1]([C:4]1[C:9]2[CH2:10][CH:11]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:12]([OH:39])([C:16]([O:18][CH3:19])=[O:17])[CH2:13][NH:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 31215Triethyl phosphiteHCID 3251421Potassium bis(trimethylsilyl)amideHCID 14156203HCID 14156203, compound

Product 1

HCID 131715563HCID 131715563, compoundYield 166.9%

Reagents, catalysts & solvents 2

HCID 977OxygenSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6-Nitro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (5.05 0.014 mol) in 250 ml of tetrahydrofuran was treated with 10.9 g (0.055 mol) of potassium hexamethyldisilazide at -70° C., then with 9.6 ml (0.056 mol) of triethyl phosphite and oxygen gas at -70 to 0° C. as described in Example 1, Method II, part D. The solution became very dark on adding the base and did not lighten on passing in oxygen. Workup according to the reference procedure gave 8.7 g of a deep red oil which did not crystallize following trituration with hexane. The final yield of a deep red oil was 5.3 g.

Workup

  1. customat -70 to 0° C.
  2. additionon adding the base

Sources & evidence

ORD record
ord-2688977cd21d414080f0ce7ce4c7d5e1
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

Loading…