HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Acetic Acid → 3beta-(Tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehyde

HRID 1708818
Notes
Print preview

Reaction equation

HRID 1708818 reaction equation
C(O)(=O)C.CC1(C)CO[CH:9]([CH:12]([C@@H:14]2[C@:31]3([CH3:32])[C@H:17]([C:18]4[C@H:28]([CH2:29][CH2:30]3)[C@:26]3([CH3:27])[C:21]([CH2:22][C@@H:23]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:24][C@@H:25]3[O:33][CH2:34][O:35][CH3:36])=[CH:20][CH:19]=4)[CH2:16][CH2:15]2)[CH3:13])[O:8]C1>O1CCCC1>[Si:38]([O:37][C@H:23]1[CH2:24][C@H:25]([O:33][CH2:34][O:35][CH3:36])[C@@:26]2([CH3:27])[C:21](=[CH:20][CH:19]=[C:18]3[C@@H:28]2[CH2:29][CH2:30][C@@:31]2([CH3:32])[C@H:17]3[CH2:16][CH2:15][C@@H:14]2[CH:12]([CH:9]=[O:8])[CH3:13])[CH2:22]1)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 6785299620-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregna-5,7-diene

Product 1

HCID 228439363beta-(Tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran was dissolved 20-(5,5-dimethyl-1,3-dioxan-2-yl)-3β-(tert-butyldimethylsilyl)oxy-1α-(methoxymethyl)oxypregna-5,7-diene, followed by addition of 5 ml of 80% acetic acid. The mixture was refluxed in an atmosphere of argon gas for 12 hours. The reaction mixture was then worked up in the same manner as Example 156 to give 50 mg of 3β-(tert-butyldimethylsilyl)oxy-1α-(methoxymethyl)oxypregna-5,7 -diene-20-carbaldehyde showing the following physical properties. 1H-NMR spectrum (90 MHz) δTMSCDCl 3: 0.13 (s, 6H), 0.66 (s, 3H), 0.95 (s, 9H), 1.01 (s, 3H), 1.14 (d, J=6.2 Hz, 3H), 3.40 (s, 3H), 4.10-4.50 (2H), 4.80 (br. s, 2H), 5.35 (m, 1H), 5.70 (m, 1H), 9.59 (d, J=3.5 Hz, 1H) IR spectrum (KBr): 1725 cm-1

Workup

  1. temperatureThe mixture was refluxed in an atmosphere of argon gas for 12 hours

Sources & evidence

ORD record
ord-fe4f2b4accef48d38e3a25f8eb3d128a
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05359055

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes