Acetyl chloride → HCID 86743523, compound

HRID 1639184Notes

Reaction equation

HRID 1639184 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]([O:5][C@@H:6]1[CH2:23][C@@:21]2([CH3:22])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:16]2[C@H:7]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15]2)=[O:4].[C:33](Cl)(=[O:35])[CH3:34].[Cl-].[Al+3].[Cl-].[Cl-].C(=O)(O)[O-].[Na+]>ClCCl>[C:33]([C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][CH2:15][C@@H:16]3[C@@H:7]([C:8]=2[CH:9]=1)[C@H:6]([O:5][C:3](=[O:4])[C:2]([CH3:32])([CH3:31])[CH3:1])[CH2:23][C@@:21]1([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]1[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 54528332HCID 54528332, compound

Product 1

HCID 86743523HCID 86743523, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the diester (26A) (42 mg, 0.095 mmol) and acetyl chloride (0.1 ml, 0.11 g, 1.41 mmol) in dry dichloromethane (1 ml) was treated with anhydrous aluminium chloride (63 mg, 0.47 mmol) at room temperature. After being stirred to 30 min, a saturated aqueous solution of sodium bicarbonate was added, and the mixture was extracted with dichloromethane and worked up in the usual manner to give an oil which was chromatographed on silica (2 g). Elution with ether-light petroleum (1:5) gave the product (27) (43 mg, 93%), as an oil, νmax 1730 and 1685 cm-1 (C=O), δ (250 MHz) 7.75 (1 H, dd, J 8 and 1.5 Hz, 3-proton), 7.64 (1 H, d, J 1.5 Hz, 1-proton), 7.20 (1 H, d, J 8 Hz, 4-proton), 5.52 (1 H, dt, J 10.5 and 5.5 Hz, 11-proton), 4.66 (1 H, dd, J 9 and 7 Hz, 17-proton), 2.89 (2 H, t, J 7 Hz, 6-protons), 2.53 (3 H, s, CH3CO), 2.37-1.25 (11 H, m), 1.23 (18 H, two s, OBut), 0.89 (3 H, s, 18-CH3), M+ (ammonia chemical iionization) 500 (M+NH3).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customto give an oil which
  3. customwas chromatographed on silica (2 g)
  4. washElution with ether-light petroleum (1:5)

Sources & evidence

ORD record
ord-aaf1bb80375341b6815c3701a7cdb2df
Source dataset
uspto-grants-1989_11
Patent number
US04882439

Reaction notes

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