Sodium hydride → HCID 86736511, compound

HRID 261867Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[C:13]2[CH:12]3[CH2:14][CH:15]([NH:18][C:19](=[O:21])[CH3:20])[CH2:16][CH2:17][CH:11]3[CH2:10][O:9][C:8]=2[CH:7]=[C:6]([CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH3:27])[CH:5]=1.[C:28](Br)(=[O:31])[CH2:29][CH3:30]>>[C:28]([O:3][C:4]1[C:13]2[CH:12]3[CH2:14][CH:15]([N:18]([C:4](=[O:3])[CH2:5][CH3:6])[C:19](=[O:21])[CH3:20])[CH2:16][CH2:17][CH:11]3[CH2:10][O:9][C:8]=2[CH:7]=[C:6]([CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH3:27])[CH:5]=1)(=[O:31])[CH2:29][CH3:30]

Participants

Reactant 3

HCID 24758Sodium hydride2×

HCID 69018Propionyl bromide

HCID 86736512HCID 86736512, compound

Product 1

HCID 86736511HCID 86736511, compound

Procedure

Exhaustive acylation of 9-amino and 9-acylaminodibenzo[b,d]pyrans effects peracylation to afford 1-acyloxy-9-diacylamino-hexahydro-dibenzo[b,d]pyrans. Such peracylation can be effected by reacting either a 9-amino or a 9-acylamino-hexahydro-dibenzo[b,d]pyran with an excess of an acylating agent, for example from about 2 to 10 molar excess, as well as carrying out the reaction at an elevated temperature of about 60° to about 150° C. The peracylation is carried out in the presence of a strong base such as sodium hydride. As an illustration of peracylation, a compound such as dl-cis-1-hydroxy-3-(2-hexenyl)-9-acetamido-6a,7,8,9,10,10a-hexahydro-6H-dibenzo[b,d]pyran can be reacted with about a 5 molar excess of propionyl bromide in the presence of sodium hydride at about 100° C. for about seventy-two hours to afford dl-cis-1-propionoxy-3-(2-hexenyl)-9-(N-propionyl)acetamido-6a,7,8,9,10,10a-hexahydro-6H-dibenzo[b,d]pyran.

Workup

customthe reaction at an elevated temperature of about 60° to about 150° C

Sources & evidence

ORD record: ord-a0a926260acf46febf4efb9789a4e13f
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04152450

Reaction notes

Loading…