Acetic Anhydride → HCID 86738626, compound

HRID 2198541Notes

Reaction equation

HRID 2198541 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]([OH:34])([CH2:8][CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@:31]2([CH3:32])[C@H:16]([C@H:17]3[C@H:28]([CH2:29][CH2:30]2)[C@:26]2([CH3:27])[C:20]([CH2:21][C@H:22]([CH2:24][C@@H:25]2[OH:33])[OH:23])=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)[CH3:12])[C:4]([F:7])([F:6])[F:5].[C:37]([O:40]C(=O)C)(=[O:39])[CH3:38]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:37]([OH:40])(=[O:39])[CH3:38].[C:37]([OH:40])(=[O:39])[CH3:38].[C:37]([OH:40])(=[O:39])[CH3:38].[F:1][C:2]([F:35])([F:36])[C:3]([OH:34])([CH2:8][CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@:31]2([CH3:32])[C@H:16]([C@H:17]3[C@H:28]([CH2:29][CH2:30]2)[C@:26]2([CH3:27])[C:20]([CH2:21][C@H:22]([CH2:24][C@@H:25]2[OH:33])[OH:23])=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)[CH3:12])[C:4]([F:5])([F:7])[F:6]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 13075708HCID 13075708, compound

Product 1

HCID 86738626HCID 86738626, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 216 mg of the triol (5) and catalytic amounts (ca 20 mg) of 4-dimethylaminopyridine in acetic anhydride (1.5 ml) and pyridine (3 ml) was stirred for 20 hr at room temperature. After the reaction mixture was concentrated in vacuo, the residue was chromatographed on silica gel (n-hexane-AcOEt, 10:1) to give 263 mg (98%) of the triacetate (6), which was dried at 70° C. (5 mm Hg) for 20 hr. 6: glass; MS m/e 592(M+ -AcOH), 532(M+ -2AcOH), 517, 413, 253; NMR(CDCl3)δ0.66(s, 18-H3, 0.94(d, J=6 Hz, 21-H), 1.10(s, 19-H3)2.03, 2.06 and 2.16(9H, each s, acetyl), 4.98(1H, m, 3-H), 5.06(1H, m, 1-H), 5.53(1H, m, 6-H).

Workup

  1. concentrationAfter the reaction mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel (n-hexane-AcOEt, 10:1)

Sources & evidence

ORD record
ord-c5c9794212034977ac4087ecd105841f
Source dataset
uspto-grants-1982_11
Patent number
US04358406

Reaction notes

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